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Digest: Synthesis of Benzaldehydes Please login to post

Aurelius
(Active Asperger Archivist)
05-19-04 17:29
No 508238
Synthesis of Benzaldehydes
(Rated as: excellent)

Synthesis of Benzaldehyde and it Substituted Analogues

Benzaldehyde Derived:

Benzaldehyde:
Post 511939 (Kinetic: "Cinnamic acid to benzaldehyde", Newbee Forum)
Post 208719 (Osmium: "Re: The easiest synth of benzaldehyde from toluene", Chemistry Discourse)
Patents Related To Link Above:
Post 208782 (PolytheneSam: "Re: The easiest synth of benzaldehyde from toluene", Chemistry Discourse)

Post 377691 (moo: "Aldehydes from Grignard reagents with formic acid", Methods Discourse)
Post 241349 (foxy2: "benzaldehyde from toluene - Additions", Chemistry Discourse)
Post 244957 (Chemikaze: "Benzaldehyde via MnO2 oxidation of toluene", Novel Discourse)
Related: Post 296395 (hest: "You need 'activated' MnO2.", Newbee Forum)
or
https://www.rhodium.ws/chemistry/oxycodone.html

Post 354314 (Rhodium: "General Method for the Preparation of ...", Chemistry Discourse) (from benzyl alcohol)

Post 479722 (lugh: "Reference Uploaded", Chemistry Discourse) (Deox. of Benzoic acid)
Post 493837 (moo: "Benzoic acid to benzaldehyde or benzene", Chemistry Discourse) (second part of deox.)

Refs for Various Methods:
Post 354361 (GC_MS: "Meyer", Chemistry Discourse)

Post 444540 (Lego: "Solventless oxidation with KMnO4/montmorillonite", Chemistry Discourse) (tol. to benz.)
Post 459026 (hermanroempp: "Just another oxidiser - Manganese-(III)-sulfate", Chemistry Discourse) (tol. to benz.)
Post 468094 (moo: "I've thought about the possibility of ...", Chemistry Discourse) (tol. to benz.)
Post 498021 (Organikum: "H2O2 toluene oxidation (vanadium catalyzed)", Chemistry Discourse) (tol. to benz.)
Post 473147 (Rhodium: "Toluene to Benzaldehyde using Co(II)-Peroxygen", Chemistry Discourse)
Post 457354 (LaBTop: "Crossposting, Hah!", Chemistry Discourse) (tol. to benz. by air ox.)
Post 471369 (halfkast: "Chomic", Chemistry Discourse) (tol. to benz. by air ox.)
http://www.sciencemadness.org/papers/toluene_air_oxidation.pdf
http://www.sciencemadness.org/papers/toluene_air_oxidation2.pdf

Post 479888 (Rhodium: "More on Toluene -> Benzaldehyde", Chemistry Discourse)

Post 458012 (Tdurden969: "References", Chemistry Discourse) (electro. to benz.)
Post 493948 (Organikum: "Benzoic acid to benzaldehyde by electrolysis", Chemistry Discourse) (benz. acid. electro.)

Post 437235 (Organikum: "B-dehyde", Stimulants) (patents)

Mono-Substituted Benzaldehydes:
Salicylaldehyde: 2-OH-
Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) (see Ref # 11)
Post 422019 (Vitus_Verdegast: "found an interesting article", Methods Discourse)

Anisaldeyde: 4-MeO
Post 382264 (Antoncho: "Zealot: azomethinic (Haack) formylation", Novel Discourse)
Post 475637 (Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse)
https://www.rhodium.ws/chemistry/me3po4.html
Post 504013 (starlight: "some interesting mandelic acid patents", Chemistry Discourse)
Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) (see ref #11)

Di-Substituted Benzaldehydes:
2-OH-3-BuO-
Post 355308 (foxy2: "More Duff Reaction", Novel Discourse)

2-OH-3-t-Amyl-
Post 355308 (foxy2: "More Duff Reaction", Novel Discourse)

2-OH-4-Me-
Post 234191 (megamole: "Re: Magnesium Alkoxides", Chemistry Discourse)

2-OH-5-Br: (5-BromoSalicylaldehyde)
Post 511284 (lugh: "5-bromosalicylaldehyde", Chemistry Discourse)

2-OH-5-Me-
Post 355308 (foxy2: "More Duff Reaction", Novel Discourse)

2-OH-5-MeO-
Post 214710 (Karl: "2-Hydroxy-5-methoxybenzaldehyde", Chemistry Discourse)
Post 511008 (demorol: "Methoxylation of various aryl bromides", Chemistry Discourse)

2,5-DiEtO-
Post 239307 (Rhodium: "Re: Syringaldehyde via Duff formylation", Novel Discourse)

2-OH-5-MeO-
Post 290438 (Lilienthal: "2-hydroxy-5-MeO-BA: The easy way", Chemistry Discourse)
Post 234191 (megamole: "Re: Magnesium Alkoxides", Chemistry Discourse)
Post 475637 (Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse)
Post 330714 (Antoncho: "A patented improvement", Chemistry Discourse)

2-OH-6-Me-
Post 234191 (megamole: "Re: Magnesium Alkoxides", Chemistry Discourse)

2,5-DiMeO-
Post 510729 (Rhodium: "Some retrievals & some bad news..", Novel Discourse)
Post 493429 (Nicodem: "HCHO/Mg(II) formylation + methylation patent", Methods Discourse)
Post 348592 (Antoncho: "Methyl iodide methylation of 2-OH-5-MeO-BA.", Chemistry Discourse)
Post 423268 (foxy2: "Synthesis of 2,5-dimethoxybenzaldehyde", Chemistry Discourse)
Post 473079 (Rhodium: "Gattermann 2,5-Dimethoxybenzaldehyde", Novel Discourse)
Post 454518 (Rhodium: "Two Syntheses of 2,5-Dimethoxybenzaldehyde", Chemistry Discourse)
Post 475637 (Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse)
Post 214710 (Karl: "2-Hydroxy-5-methoxybenzaldehyde", Chemistry Discourse)
https://www.rhodium.ws/chemistry/me3po4.html
The following procedure is NOT valid:
Post 70528 (karel: "Synth of 2,5-dimethoxybenzaldehyde", Serious Chemistry) (must also read Post 299121 (karel: "Revision of post 70528", Chemistry Discourse))

Veratraldehyde: 3,4-DiMeO-
http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0619

Protocatechualdehyde: 3,4-DiOH-
Post 477628 (Rhodium: "Vanillin to Protocatechualdehyde (AlCl3/Py)", Methods Discourse)
https://www.rhodium.ws/chemistry/methylenation.html

Bourbonal: 3-EtO-4-OH-

3,5-DiMeO-
Post 473076 (Rhodium: "Benzoic Acids to Benzaldehydes", Chemistry Discourse)

Vanillin: 4-OH-3-MeO-
Post 275285 (foxy2: "5-Br-Vanillin Methoxylation (CuBr/EtOAc/NaOMe)", Chemistry Discourse) (or the direct link below)
http://valhalla.chem.udel.edu/vanillin.html
Post 286983 (foxy2: "Hmmm, CO2????", Chemistry Discourse)
Post 504013 (starlight: "some interesting mandelic acid patents", Chemistry Discourse)
Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) (see ref # 11)
Post 211048 (Rhodium: "Re: Vanillin from OTC Vanilla Extract", Chemistry Discourse)
Post 511008 (demorol: "Methoxylation of various aryl bromides", Chemistry Discourse)

3-Alkoxy-4-OH-
Post 504013 (starlight: "some interesting mandelic acid patents", Chemistry Discourse)

4-EtO-3-MeO-
https://www.rhodium.ws/chemistry/me3po4.html

Tri-Substituted Benzaldehydes:
2-Bromo-3,4-DiMeO-
Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)
Post 214376 (foxy2: "Re: 2 Bromination of 3,4-dimethoxybenzaldehyde", Chemistry Discourse)

2-OH-3,5-DiBr
Post 355308 (foxy2: "More Duff Reaction", Novel Discourse)

2-OH-3,5-Di-t-Bu- (also: 3,5-Di-t-Bu-Salicylaldehyde)
Post 355308 (foxy2: "More Duff Reaction", Novel Discourse)

2-OH-3-Cl-5-t-Bu
Post 355308 (foxy2: "More Duff Reaction", Novel Discourse)

2-OH-3-Me-5-t-Amyl
Post 355308 (foxy2: "More Duff Reaction", Novel Discourse)

2,3,5-TriMeO-
Post 494386 (Rhodium: "Synthesis of TMA-2 Precursors from Vanillin", Novel Discourse)
https://www.rhodium.ws/chemistry/me3po4.html

2-OH-3-MeO-5-Me-
Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)

2-BromoVanillin: 2-Br-3-MeO-4-OH-
Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)

2-Br-4,5-DiMeO-
Post 214369 (foxy2: "2 Bromination of 3,4-dimethoxybenzaldehyde", Chemistry Discourse)

Asarylaldehyde: 2,4,5-TriMeO-
https://www.rhodium.ws/chemistry/me3po4.html
Post 471601 (Rhodium: "Indirect 6-Methoxylation of Veratraldehyde", Methods Discourse)

2,4,6-TriMeO-
Post 480958 (hest: "Synt of 2,4,6-trimethoxybenzaldehyde", Chemistry Discourse)
Post 481038 (Rhodium: "Synthesis of 2,4,6-Trimethoxybenzaldehyde", Chemistry Discourse)

2,5-DiMeO-3-Me-
Post 300201 (Antoncho: "3-methyl-2,5-diMeO-benzaldehyde", Novel Discourse)
https://www.rhodium.ws/chemistry/methyldimethoxybenzaldehydes.html

2,5-DiMeO-4-Me-
https://www.rhodium.ws/chemistry/methyldimethoxybenzaldehydes.html

3,4-DiMeO-5-OH-
Post 506221 (Mephisto: "Synthesis of 3,4-dimethoxy-5-hydroxybenzaldehyde", Chemistry Discourse)

3,4,5-TriMeO-
Post 501059 (ning: "TRANSLATED: Chinese 3,4,5 TMB article", Methods Discourse)
Post 507150 (Rhodium: "3,4,5-Trimethoxybenzaldehyde from Gallic Acid", Methods Discourse)
https://www.rhodium.ws/chemistry/345-tmb.html
https://www.rhodium.ws/chemistry/me3po4.html

3,4,6-TriMeO-
Post 464340 (imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse)

6-BromoVanillin: 3-MeO-4-OH-6-Br-
Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)

3-DiMe-2-OH-
Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)

3,5-Bis(DiMeAminoMe)-2-OH-
Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)

3,5-DiBr-4-OH-
Post 275643 (Antoncho: "Syringaldehyde from p-cresol in two steps", Chemistry Discourse)

3,5-DiMe-4-OH-
Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)

3,5-DiMeO-4-OH-
Post 275269 (Antoncho: "Re: Vanillin", Chemistry Discourse)

3,5-Bis(DiMeAminoMe)-4-OH-
Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)

3,5-Di-t-Bu-4-OH-
Post 208298 (Antoncho: "Duff formylation in aq. AcOH - 90% yield :))", Chemistry Discourse)

4-I-2,5-DiMeO-
Post 422838 (GC_MS: "1-(4-iodo-2,5-dimethoxyphenyl)-2-propanone", Methods Discourse)
Post 469528 (Chimimanie: "halogenation of 2,5-DMB & benzonitrile + DOI ?", Methods Discourse)

4-Cl-2,5-DiMeO-
Post 106232 (rev drone: "Iodination via NIS -- various conditions", Chemistry Discourse)
Post 482940 (Lego: "Duff formylation of 2-chloro-1,4-dimethoxybenzene", Chemistry Discourse)

4-Br-2,5-DiMeO-
Post 106232 (rev drone: "Iodination via NIS -- various conditions", Chemistry Discourse)
Post 469528 (Chimimanie: "halogenation of 2,5-DMB & benzonitrile + DOI ?", Methods Discourse)
Post 468077 (moo: "Oxidations and brominations w/ H2O2/Br2/HBr", Methods Discourse)
Post 468078 (moo: "Oxidations and brominations w/ H2O2/Br2/HBr", Methods Discourse)

5-NO₂-2,3-DiMeO-
Post 425432 (Vitus_Verdegast: "J. Chem. Soc. (1923) 123, page 1587 and 1588", Methods Discourse)

5-NO₂-2-MeO-3-EtO-
Post 425432 (Vitus_Verdegast: "J. Chem. Soc. (1923) 123, page 1587 and 1588", Methods Discourse)

Syringaldehyde: 4-OH-3,5-DiMeO-
Post 355336 (Antoncho: "Another EXCELLENT formylation!", Novel Discourse)
Post 275285 (foxy2: "5-Br-Vanillin Methoxylation (CuBr/EtOAc/NaOMe)", Chemistry Discourse)
https://www.rhodium.ws/chemistry/345-tmb.html
Post 275643 (Antoncho: "Syringaldehyde from p-cresol in two steps", Chemistry Discourse)
Post 286983 (foxy2: "Hmmm, CO2????", Chemistry Discourse)
Post 235806 (Osmium: "Re: Magnesium Alkoxides", Chemistry Discourse) (as seen in https://www.rhodium.ws/chemistry/mmda.mescaline.html )
Post 239082 (Antoncho: "Syringaldehyde via Duff formylation", Novel Discourse)
Post 511008 (demorol: "Methoxylation of various aryl bromides", Chemistry Discourse)

4-OH-5-MeO-3-Me- (aka: 5-Me-Vanillin)
Post 253386 (slothrop: "5-Methyl-MDA", Novel Discourse)

4-OH-5-Me-3-MeO-
Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)

4,5-DiOH-3-Me-
Post 253386 (slothrop: "5-Methyl-MDA", Novel Discourse)

5-DiMeAminoMe-2-OH-3-MeO-
Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)

5-Bromo-3-DiMeo-
Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)

5-DiMeAminoMe-4-OH-3-MeO-
Post 253386 (slothrop: "5-Methyl-MDA", Novel Discourse)
Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)

Higher-Poly-Substituted Benzaldehydes:
2-OH-3-i-Pro-5-Cl-6-Me-
Post 355308 (foxy2: "More Duff Reaction", Novel Discourse)

2,5-DiMeO-3,6-DiMe-
Post 472752 (Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)

2,3,4-TriMeO-3,6-DiMe-
Post 472752 (Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)

2,4,5-TriMeO-3,6-DiMe-
Post 472752 (Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)

4-OH-2,5-DiMeo-3,6-DiMe-
Post 472752 (Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)

Piperonal Derived:

Piperonal (Heliotropine): 3,4-MD-Benz.
Post 463350 (Antoncho: "A great piperonal patent", Novel Discourse)
Post 391475 (pHarmacist: "One More piperonal patent, High-yielding", Novel Discourse)
Post 328397 (demorol: "Piperonal synthesis", Novel Discourse)
Post 329015 (demorol: "More patents", Novel Discourse)
Post 382264 (Antoncho: "Zealot: azomethinic (Haack) formylation", Novel Discourse)

5-OH-
Post 504409 (Rhodium: "5-Hydroxypiperonal and Myristicinaldehyde", Novel Discourse)
Also: https://www.rhodium.ws/chemistry/5-hydroxy-piperonal.shulgin.html

5-Br-
Post 507151 (Rhodium: "Synthesis of 5-Bromopiperonal", Methods Discourse)

5-Me-
Post 253386 (slothrop: "5-Methyl-MDA", Novel Discourse)

6-OH-
Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)

6-NH₂-
Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)

6-NO₂-
Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)

2-Br-6-MeO-
Post 507151 (Rhodium: "Synthesis of 5-Bromopiperonal", Methods Discourse)

1-MeO-2,3-MD-
Post 484717 (Rhodium: "Croweacinaldehyde & Isomers", Novel Discourse)

2,3-MD-4-MeO-
Post 464340 (imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse)
Post 484717 (Rhodium: "Croweacinaldehyde & Isomers", Novel Discourse)

Croweacinaldehyde: 2-MeO-3,4-MD-
Post 484271 (Rhodium: "Croweacinaldehyde from Pyrogallol (55%)", Novel Discourse)
Post 484720 (Rhodium: "Croweacinaldehyde", Novel Discourse)
Post 464340 (imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse)
Post 245205 (Rhodium: "Re: Benzaldehyde Of Croweacin?", Chemistry Discourse)
Post 484717 (Rhodium: "Croweacinaldehyde & Isomers", Novel Discourse)

2-Alkoxy-4,5-MD-
Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)

Carpacinaldehyde: 2-MeO-4,5-MD-
Post 247833 (Rhodium: "Carpacin isolation & Physical Data", Chemistry Discourse)
Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)

Apiolaldehyde: 2,5-DiMeO-3,4-MD-
Post 489559 (Rhodium: "Synthesis of Myristicinaldehyde/Apiolealdehyde", Novel Discourse)
https://www.rhodium.ws/chemistry/myristicinaldehyde.shulgin.html

Myristicinaldehyde: 3-MeO-3,4-MD-
Post 509800 (Rhodium: "Myristicin Derivatives", Novel Discourse)
Post 508799 (Wraith: "Methylenation without KF or PTC", Novel Discourse)
Post 504409 (Rhodium: "5-Hydroxypiperonal and Myristicinaldehyde", Novel Discourse)
Also: https://www.rhodium.ws/chemistry/5-hydroxy-piperonal.shulgin.html
Post 489659 (Rhodium: "Myristicin & Myristicinaldehyde", Novel Discourse)
IR of Myristicin
Post 494937 (Islamybad: "Here's the IR spectrum of myristicin from two...", Serious Chemistry)
Post 452949 (GC_MS: "myristicinaldehyde", Chemistry Discourse)(see warning below before attempting this synthesis:)

Warning about TetraNitroMethane and Relatives:
Post 355957 (GC_MS: "How dangerous is tetranitromethane?", Chemistry Discourse)

3,4-MD-6-OH-
Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)

6-OH-2-MeO-3,4-MD-
Post 484717 (Rhodium: "Croweacinaldehyde & Isomers", Novel Discourse)

General Aldehyde Synthesis or those containing large numbers of aldehyde products:

https://www.rhodium.ws/chemistry/formylations.html
Post 355321 (foxy2: "formylation by the "nitroso" method", Novel Discourse)
Post 355336 (Antoncho: "Another EXCELLENT formylation!", Novel Discourse)
Post 235460 (Antoncho: "Re: Formylations", Chemistry Discourse)
Post 422033 (Vitus_Verdegast: "R-T articles that might be interesting", Methods Discourse)
https://www.rhodium.ws/pdf/bromo2hydroxy-benzaldehydes.pdf

Side Notes:
Formylation Mechanism:
Post 481046 (Rhodium: "Magnesium ortho-Formylation Mechanism", Methods Discourse) smile

Several Naturally Occuring Aldehydes:
https://www.rhodium.ws/chemistry/me3po4.html

Act quickly or not at all.

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		Aurelius (Active Asperger Archivist) 05-19-04 17:29 No 508238				Synthesis of Benzaldehydes (Rated as: excellent)
						Synthesis of Benzaldehyde and it Substituted Analogues Benzaldehyde Derived: Benzaldehyde: Post 511939 (Kinetic: "Cinnamic acid to benzaldehyde", Newbee Forum) Post 208719 (Osmium: "Re: The easiest synth of benzaldehyde from toluene", Chemistry Discourse) Patents Related To Link Above: Post 208782 (PolytheneSam: "Re: The easiest synth of benzaldehyde from toluene", Chemistry Discourse) Post 377691 (moo: "Aldehydes from Grignard reagents with formic acid", Methods Discourse) Post 241349 (foxy2: "benzaldehyde from toluene - Additions", Chemistry Discourse) Post 244957 (Chemikaze: "Benzaldehyde via MnO2 oxidation of toluene", Novel Discourse) Related: Post 296395 (hest: "You need 'activated' MnO2.", Newbee Forum) or https://www.rhodium.ws/chemistry/oxycodone.html Post 354314 (Rhodium: "General Method for the Preparation of ...", Chemistry Discourse) (from benzyl alcohol) Post 479722 (lugh: "Reference Uploaded", Chemistry Discourse) (Deox. of Benzoic acid) Post 493837 (moo: "Benzoic acid to benzaldehyde or benzene", Chemistry Discourse) (second part of deox.) Refs for Various Methods: Post 354361 (GC_MS: "Meyer", Chemistry Discourse) Post 444540 (Lego: "Solventless oxidation with KMnO4/montmorillonite", Chemistry Discourse) (tol. to benz.) Post 459026 (hermanroempp: "Just another oxidiser - Manganese-(III)-sulfate", Chemistry Discourse) (tol. to benz.) Post 468094 (moo: "I've thought about the possibility of ...", Chemistry Discourse) (tol. to benz.) Post 498021 (Organikum: "H2O2 toluene oxidation (vanadium catalyzed)", Chemistry Discourse) (tol. to benz.) Post 473147 (Rhodium: "Toluene to Benzaldehyde using Co(II)-Peroxygen", Chemistry Discourse) Post 457354 (LaBTop: "Crossposting, Hah!", Chemistry Discourse) (tol. to benz. by air ox.) Post 471369 (halfkast: "Chomic", Chemistry Discourse) (tol. to benz. by air ox.) http://www.sciencemadness.org/papers/toluene_air_oxidation.pdf http://www.sciencemadness.org/papers/toluene_air_oxidation2.pdf Post 479888 (Rhodium: "More on Toluene -> Benzaldehyde", Chemistry Discourse) Post 458012 (Tdurden969: "References", Chemistry Discourse) (electro. to benz.) Post 493948 (Organikum: "Benzoic acid to benzaldehyde by electrolysis", Chemistry Discourse) (benz. acid. electro.) Post 437235 (Organikum: "B-dehyde", Stimulants) (patents) Mono-Substituted Benzaldehydes: Salicylaldehyde: 2-OH- Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) (see Ref # 11) Post 422019 (Vitus_Verdegast: "found an interesting article", Methods Discourse) Anisaldeyde: 4-MeO Post 382264 (Antoncho: "Zealot: azomethinic (Haack) formylation", Novel Discourse) Post 475637 (Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse) https://www.rhodium.ws/chemistry/me3po4.html Post 504013 (starlight: "some interesting mandelic acid patents", Chemistry Discourse) Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) (see ref #11) Di-Substituted Benzaldehydes: 2-OH-3-BuO- Post 355308 (foxy2: "More Duff Reaction", Novel Discourse) 2-OH-3-t-Amyl- Post 355308 (foxy2: "More Duff Reaction", Novel Discourse) 2-OH-4-Me- Post 234191 (megamole: "Re: Magnesium Alkoxides", Chemistry Discourse) 2-OH-5-Br: (5-BromoSalicylaldehyde) Post 511284 (lugh: "5-bromosalicylaldehyde", Chemistry Discourse) 2-OH-5-Me- Post 355308 (foxy2: "More Duff Reaction", Novel Discourse) 2-OH-5-MeO- Post 214710 (Karl: "2-Hydroxy-5-methoxybenzaldehyde", Chemistry Discourse) Post 511008 (demorol: "Methoxylation of various aryl bromides", Chemistry Discourse) 2,5-DiEtO- Post 239307 (Rhodium: "Re: Syringaldehyde via Duff formylation", Novel Discourse) 2-OH-5-MeO- Post 290438 (Lilienthal: "2-hydroxy-5-MeO-BA: The easy way", Chemistry Discourse) Post 234191 (megamole: "Re: Magnesium Alkoxides", Chemistry Discourse) Post 475637 (Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse) Post 330714 (Antoncho: "A patented improvement", Chemistry Discourse) 2-OH-6-Me- Post 234191 (megamole: "Re: Magnesium Alkoxides", Chemistry Discourse) 2,5-DiMeO- Post 510729 (Rhodium: "Some retrievals & some bad news..", Novel Discourse) Post 493429 (Nicodem: "HCHO/Mg(II) formylation + methylation patent", Methods Discourse) Post 348592 (Antoncho: "Methyl iodide methylation of 2-OH-5-MeO-BA.", Chemistry Discourse) Post 423268 (foxy2: "Synthesis of 2,5-dimethoxybenzaldehyde", Chemistry Discourse) Post 473079 (Rhodium: "Gattermann 2,5-Dimethoxybenzaldehyde", Novel Discourse) Post 454518 (Rhodium: "Two Syntheses of 2,5-Dimethoxybenzaldehyde", Chemistry Discourse) Post 475637 (Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse) Post 214710 (Karl: "2-Hydroxy-5-methoxybenzaldehyde", Chemistry Discourse) https://www.rhodium.ws/chemistry/me3po4.html The following procedure is NOT valid: Post 70528 (karel: "Synth of 2,5-dimethoxybenzaldehyde", Serious Chemistry) (must also read Post 299121 (karel: "Revision of post 70528", Chemistry Discourse)) Veratraldehyde: 3,4-DiMeO- http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0619 Protocatechualdehyde: 3,4-DiOH- Post 477628 (Rhodium: "Vanillin to Protocatechualdehyde (AlCl3/Py)", Methods Discourse) https://www.rhodium.ws/chemistry/methylenation.html Bourbonal: 3-EtO-4-OH- 3,5-DiMeO- Post 473076 (Rhodium: "Benzoic Acids to Benzaldehydes", Chemistry Discourse) Vanillin: 4-OH-3-MeO- Post 275285 (foxy2: "5-Br-Vanillin Methoxylation (CuBr/EtOAc/NaOMe)", Chemistry Discourse) (or the direct link below) http://valhalla.chem.udel.edu/vanillin.html Post 286983 (foxy2: "Hmmm, CO2????", Chemistry Discourse) Post 504013 (starlight: "some interesting mandelic acid patents", Chemistry Discourse) Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) (see ref # 11) Post 211048 (Rhodium: "Re: Vanillin from OTC Vanilla Extract", Chemistry Discourse) Post 511008 (demorol: "Methoxylation of various aryl bromides", Chemistry Discourse) 3-Alkoxy-4-OH- Post 504013 (starlight: "some interesting mandelic acid patents", Chemistry Discourse) 4-EtO-3-MeO- https://www.rhodium.ws/chemistry/me3po4.html Tri-Substituted Benzaldehydes: 2-Bromo-3,4-DiMeO- Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) Post 214376 (foxy2: "Re: 2 Bromination of 3,4-dimethoxybenzaldehyde", Chemistry Discourse) 2-OH-3,5-DiBr Post 355308 (foxy2: "More Duff Reaction", Novel Discourse) 2-OH-3,5-Di-t-Bu- (also: 3,5-Di-t-Bu-Salicylaldehyde) Post 355308 (foxy2: "More Duff Reaction", Novel Discourse) 2-OH-3-Cl-5-t-Bu Post 355308 (foxy2: "More Duff Reaction", Novel Discourse) 2-OH-3-Me-5-t-Amyl Post 355308 (foxy2: "More Duff Reaction", Novel Discourse) 2,3,5-TriMeO- Post 494386 (Rhodium: "Synthesis of TMA-2 Precursors from Vanillin", Novel Discourse) https://www.rhodium.ws/chemistry/me3po4.html 2-OH-3-MeO-5-Me- Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse) 2-BromoVanillin: 2-Br-3-MeO-4-OH- Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) 2-Br-4,5-DiMeO- Post 214369 (foxy2: "2 Bromination of 3,4-dimethoxybenzaldehyde", Chemistry Discourse) Asarylaldehyde: 2,4,5-TriMeO- https://www.rhodium.ws/chemistry/me3po4.html Post 471601 (Rhodium: "Indirect 6-Methoxylation of Veratraldehyde", Methods Discourse) 2,4,6-TriMeO- Post 480958 (hest: "Synt of 2,4,6-trimethoxybenzaldehyde", Chemistry Discourse) Post 481038 (Rhodium: "Synthesis of 2,4,6-Trimethoxybenzaldehyde", Chemistry Discourse) 2,5-DiMeO-3-Me- Post 300201 (Antoncho: "3-methyl-2,5-diMeO-benzaldehyde", Novel Discourse) https://www.rhodium.ws/chemistry/methyldimethoxybenzaldehydes.html 2,5-DiMeO-4-Me- https://www.rhodium.ws/chemistry/methyldimethoxybenzaldehydes.html 3,4-DiMeO-5-OH- Post 506221 (Mephisto: "Synthesis of 3,4-dimethoxy-5-hydroxybenzaldehyde", Chemistry Discourse) 3,4,5-TriMeO- Post 501059 (ning: "TRANSLATED: Chinese 3,4,5 TMB article", Methods Discourse) Post 507150 (Rhodium: "3,4,5-Trimethoxybenzaldehyde from Gallic Acid", Methods Discourse) https://www.rhodium.ws/chemistry/345-tmb.html https://www.rhodium.ws/chemistry/me3po4.html 3,4,6-TriMeO- Post 464340 (imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse) 6-BromoVanillin: 3-MeO-4-OH-6-Br- Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) 3-DiMe-2-OH- Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse) 3,5-Bis(DiMeAminoMe)-2-OH- Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse) 3,5-DiBr-4-OH- Post 275643 (Antoncho: "Syringaldehyde from p-cresol in two steps", Chemistry Discourse) 3,5-DiMe-4-OH- Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse) 3,5-DiMeO-4-OH- Post 275269 (Antoncho: "Re: Vanillin", Chemistry Discourse) 3,5-Bis(DiMeAminoMe)-4-OH- Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse) 3,5-Di-t-Bu-4-OH- Post 208298 (Antoncho: "Duff formylation in aq. AcOH - 90% yield :))", Chemistry Discourse) 4-I-2,5-DiMeO- Post 422838 (GC_MS: "1-(4-iodo-2,5-dimethoxyphenyl)-2-propanone", Methods Discourse) Post 469528 (Chimimanie: "halogenation of 2,5-DMB & benzonitrile + DOI ?", Methods Discourse) 4-Cl-2,5-DiMeO- Post 106232 (rev drone: "Iodination via NIS -- various conditions", Chemistry Discourse) Post 482940 (Lego: "Duff formylation of 2-chloro-1,4-dimethoxybenzene", Chemistry Discourse) 4-Br-2,5-DiMeO- Post 106232 (rev drone: "Iodination via NIS -- various conditions", Chemistry Discourse) Post 469528 (Chimimanie: "halogenation of 2,5-DMB & benzonitrile + DOI ?", Methods Discourse) Post 468077 (moo: "Oxidations and brominations w/ H2O2/Br2/HBr", Methods Discourse) Post 468078 (moo: "Oxidations and brominations w/ H2O2/Br2/HBr", Methods Discourse) 5-NO₂-2,3-DiMeO- Post 425432 (Vitus_Verdegast: "J. Chem. Soc. (1923) 123, page 1587 and 1588", Methods Discourse) 5-NO₂-2-MeO-3-EtO- Post 425432 (Vitus_Verdegast: "J. Chem. Soc. (1923) 123, page 1587 and 1588", Methods Discourse) Syringaldehyde: 4-OH-3,5-DiMeO- Post 355336 (Antoncho: "Another EXCELLENT formylation!", Novel Discourse) Post 275285 (foxy2: "5-Br-Vanillin Methoxylation (CuBr/EtOAc/NaOMe)", Chemistry Discourse) https://www.rhodium.ws/chemistry/345-tmb.html Post 275643 (Antoncho: "Syringaldehyde from p-cresol in two steps", Chemistry Discourse) Post 286983 (foxy2: "Hmmm, CO2????", Chemistry Discourse) Post 235806 (Osmium: "Re: Magnesium Alkoxides", Chemistry Discourse) (as seen in https://www.rhodium.ws/chemistry/mmda.mescaline.html ) Post 239082 (Antoncho: "Syringaldehyde via Duff formylation", Novel Discourse) Post 511008 (demorol: "Methoxylation of various aryl bromides", Chemistry Discourse) 4-OH-5-MeO-3-Me- (aka: 5-Me-Vanillin) Post 253386 (slothrop: "5-Methyl-MDA", Novel Discourse) 4-OH-5-Me-3-MeO- Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse) 4,5-DiOH-3-Me- Post 253386 (slothrop: "5-Methyl-MDA", Novel Discourse) 5-DiMeAminoMe-2-OH-3-MeO- Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse) 5-Bromo-3-DiMeo- Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) 5-DiMeAminoMe-4-OH-3-MeO- Post 253386 (slothrop: "5-Methyl-MDA", Novel Discourse) Post 486611 (Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse) Higher-Poly-Substituted Benzaldehydes: 2-OH-3-i-Pro-5-Cl-6-Me- Post 355308 (foxy2: "More Duff Reaction", Novel Discourse) 2,5-DiMeO-3,6-DiMe- Post 472752 (Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse) 2,3,4-TriMeO-3,6-DiMe- Post 472752 (Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse) 2,4,5-TriMeO-3,6-DiMe- Post 472752 (Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse) 4-OH-2,5-DiMeo-3,6-DiMe- Post 472752 (Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse) Piperonal Derived: Piperonal (Heliotropine): 3,4-MD-Benz. Post 463350 (Antoncho: "A great piperonal patent", Novel Discourse) Post 391475 (pHarmacist: "One More piperonal patent, High-yielding", Novel Discourse) Post 328397 (demorol: "Piperonal synthesis", Novel Discourse) Post 329015 (demorol: "More patents", Novel Discourse) Post 382264 (Antoncho: "Zealot: azomethinic (Haack) formylation", Novel Discourse) 5-OH- Post 504409 (Rhodium: "5-Hydroxypiperonal and Myristicinaldehyde", Novel Discourse) Also: https://www.rhodium.ws/chemistry/5-hydroxy-piperonal.shulgin.html 5-Br- Post 507151 (Rhodium: "Synthesis of 5-Bromopiperonal", Methods Discourse) 5-Me- Post 253386 (slothrop: "5-Methyl-MDA", Novel Discourse) 6-OH- Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse) 6-NH₂- Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse) 6-NO₂- Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse) 2-Br-6-MeO- Post 507151 (Rhodium: "Synthesis of 5-Bromopiperonal", Methods Discourse) 1-MeO-2,3-MD- Post 484717 (Rhodium: "Croweacinaldehyde & Isomers", Novel Discourse) 2,3-MD-4-MeO- Post 464340 (imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse) Post 484717 (Rhodium: "Croweacinaldehyde & Isomers", Novel Discourse) Croweacinaldehyde: 2-MeO-3,4-MD- Post 484271 (Rhodium: "Croweacinaldehyde from Pyrogallol (55%)", Novel Discourse) Post 484720 (Rhodium: "Croweacinaldehyde", Novel Discourse) Post 464340 (imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse) Post 245205 (Rhodium: "Re: Benzaldehyde Of Croweacin?", Chemistry Discourse) Post 484717 (Rhodium: "Croweacinaldehyde & Isomers", Novel Discourse) 2-Alkoxy-4,5-MD- Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse) Carpacinaldehyde: 2-MeO-4,5-MD- Post 247833 (Rhodium: "Carpacin isolation & Physical Data", Chemistry Discourse) Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse) Apiolaldehyde: 2,5-DiMeO-3,4-MD- Post 489559 (Rhodium: "Synthesis of Myristicinaldehyde/Apiolealdehyde", Novel Discourse) https://www.rhodium.ws/chemistry/myristicinaldehyde.shulgin.html Myristicinaldehyde: 3-MeO-3,4-MD- Post 509800 (Rhodium: "Myristicin Derivatives", Novel Discourse) Post 508799 (Wraith: "Methylenation without KF or PTC", Novel Discourse) Post 504409 (Rhodium: "5-Hydroxypiperonal and Myristicinaldehyde", Novel Discourse) Also: https://www.rhodium.ws/chemistry/5-hydroxy-piperonal.shulgin.html Post 489659 (Rhodium: "Myristicin & Myristicinaldehyde", Novel Discourse) IR of Myristicin Post 494937 (Islamybad: "Here's the IR spectrum of myristicin from two...", Serious Chemistry) Post 452949 (GC_MS: "myristicinaldehyde", Chemistry Discourse)(see warning below before attempting this synthesis:) Warning about TetraNitroMethane and Relatives: Post 355957 (GC_MS: "How dangerous is tetranitromethane?", Chemistry Discourse) 3,4-MD-6-OH- Post 464339 (imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse) 6-OH-2-MeO-3,4-MD- Post 484717 (Rhodium: "Croweacinaldehyde & Isomers", Novel Discourse) General Aldehyde Synthesis or those containing large numbers of aldehyde products: https://www.rhodium.ws/chemistry/formylations.html Post 355321 (foxy2: "formylation by the "nitroso" method", Novel Discourse) Post 355336 (Antoncho: "Another EXCELLENT formylation!", Novel Discourse) Post 235460 (Antoncho: "Re: Formylations", Chemistry Discourse) Post 422033 (Vitus_Verdegast: "R-T articles that might be interesting", Methods Discourse) https://www.rhodium.ws/pdf/bromo2hydroxy-benzaldehydes.pdf Side Notes: Formylation Mechanism: Post 481046 (Rhodium: "Magnesium ortho-Formylation Mechanism", Methods Discourse) Several Naturally Occuring Aldehydes: https://www.rhodium.ws/chemistry/me3po4.html Act quickly or not at all.