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Digest: O-Alkylation Agents: Synthesis and Use Please login to post

Aurelius
(Active Asperger Archivist)
06-06-04 00:33
No 511704
O-Alkylation Agents: Synthesis and Use
(Rated as: excellent)

O-Alkylation Agents: Synthesis and Use:

This digest will cover Methylating agents as the sole alkylating agent, unless a particular agent or reagent is novel enough to include it.

Methyl Halides:
MeI:
Examples of use:
Post 486065 (Wraith: "Selective methylation of 5-OH-Vanillin with CH3I", Chemistry Discourse)(whole thread)
Post 484676 (Rhodium: "Phenol Alkylation using Cs2CO3 as base", Novel Discourse)
Post 498502 (demorol: "Alkylation of Phenols in Water w/PTC", Novel Discourse)

Note that only MeI is used in the reactions here as a result of the gas phase conditions that the other halides adopt at standard conditions. This makes handling too hard for non-industrial preparations.

Methyl Tosylate
Post 417550 (Antoncho: "Methyl tosylate: _finally_ , OTC!!!", Novel Discourse)
Post 466982 (psyloxy: "practical alkyl tosylate synth - new approaches", Novel Discourse)
Post 505605 (psyloxy: "the important parts", Chemistry Discourse)
Post 461039 (psyloxy: "Ethyl toluenesulfonate from TsOH/ CH2(COOEt)2, 50%", Chemistry Discourse)

Dimethylsulfate: DMS
Examples of use:
Post 507716 (GC_MS: "Permethylation of pyrogallol with DMS", Methods Discourse)
Post 508168 (GC_MS: "Methylation of p-methoxyphenol with DMS", Methods Discourse)

Dimethylcarbonate: DMC
Post 426189 (Vitus_Verdegast: "Methylation of phenols using DMC and a PTC", Novel Discourse)
Post 432395 (Lego: "Methylation of phenol w/ DMC-derivates w/o PTC Pt1", Novel Discourse)( read next post in thread for rest)

Methyl ethers of N-trifluoroacetyl- and N-(m-trifluoromethyl) phenylsulfonyl-6-nitro-tyrosine t-butyl ester
Post 506741 (Rhodium: "O-Methylation of Phenolic Phenethylamine", Chemistry Discourse)

Diazomethane:
Prep and Use:
Warning: Diazomethane is a very dangerous substance (explosive) and must be properly researched before use.
Post 288566 (Antoncho: "Diazomethane. Methylations with diazomethane.", Novel Discourse)
Post 484470 (Vitus_Verdegast: "Preparation of diazomethane solutions", Novel Discourse)
Post 484552 (Rhodium: "Diazald Diazomethane", Novel Discourse)

Dimethyloxalate:DMO
Mentioned only:
Post 503306 (ning: "Try dimethyl oxalate", Novel Discourse)

Betaine
Post 412790 (Lego: "Betaine for O-methylation of Phenols", Novel Discourse)

Trimethylphosphate:TMP
https://www.rhodium.ws/chemistry/me3po4.html
Post 478120 (Vitus_Verdegast: "To avoid having to make DMS", Methods Discourse) (multiple links on this post)

MeOH: (yes, Methanol)
Post 421068 (Mountain_Girl: "P-MeO Phenol abstracts 1980-1999 #1", Methods Discourse) (one example is at reflux)

NaMeSO₄: Sodium Methylsulfate
Post 256342 (Antoncho: "Methylation of hydroquinone w/NaMeSO4: good news!", Novel Discourse)
Post 218431 (PolytheneSam: "Re: ArOR, Alternatives to dimethyl sulfate", Novel Discourse)

KMeSO₄:Potassium Methylsulfate
Post 229389 (PolytheneSam: "Re: ArOR, Alternatives to dimethyl sulfate", Novel Discourse)

Phenyltrimethylammonium Chloride
Post 443586 (Lego: "O-Methylation with Phenyltrimethylammonium chlorid", Novel Discourse)

Random patents about O-Alkylation:
Post 221040 (PolytheneSam: "Re: ArOR, Alternatives to dimethyl sulfate", Novel Discourse)

Trimethyloxonium Fluoroborate
Post 467042 (zealot: "TRIETHYLOXONIUM FLUOBORATE", Novel Discourse) (exotic, but interesting)

Gramine
(not for the usual phenolic alkylation, this is for tryptamine chemistry)
Post 495965 (Nicodem: "The papers mentioned in the above post", Tryptamine Chemistry)

Special thanks to Lego for offering help and showing interest in this project.

Act quickly or not at all.

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			Digest: O-Alkylation Agents: Synthesis and Use		Please login to post


		Aurelius (Active Asperger Archivist) 06-06-04 00:33 No 511704				O-Alkylation Agents: Synthesis and Use (Rated as: excellent)
						O-Alkylation Agents: Synthesis and Use: This digest will cover Methylating agents as the sole alkylating agent, unless a particular agent or reagent is novel enough to include it. Methyl Halides: MeI: Examples of use: Post 486065 (Wraith: "Selective methylation of 5-OH-Vanillin with CH3I", Chemistry Discourse)(whole thread) Post 484676 (Rhodium: "Phenol Alkylation using Cs2CO3 as base", Novel Discourse) Post 498502 (demorol: "Alkylation of Phenols in Water w/PTC", Novel Discourse) Note that only MeI is used in the reactions here as a result of the gas phase conditions that the other halides adopt at standard conditions. This makes handling too hard for non-industrial preparations. Methyl Tosylate Post 417550 (Antoncho: "Methyl tosylate: _finally_ , OTC!!!", Novel Discourse) Post 466982 (psyloxy: "practical alkyl tosylate synth - new approaches", Novel Discourse) Post 505605 (psyloxy: "the important parts", Chemistry Discourse) Post 461039 (psyloxy: "Ethyl toluenesulfonate from TsOH/ CH2(COOEt)2, 50%", Chemistry Discourse) Dimethylsulfate: DMS Examples of use: Post 507716 (GC_MS: "Permethylation of pyrogallol with DMS", Methods Discourse) Post 508168 (GC_MS: "Methylation of p-methoxyphenol with DMS", Methods Discourse) Dimethylcarbonate: DMC Post 426189 (Vitus_Verdegast: "Methylation of phenols using DMC and a PTC", Novel Discourse) Post 432395 (Lego: "Methylation of phenol w/ DMC-derivates w/o PTC Pt1", Novel Discourse)( read next post in thread for rest) Methyl ethers of N-trifluoroacetyl- and N-(m-trifluoromethyl) phenylsulfonyl-6-nitro-tyrosine t-butyl ester Post 506741 (Rhodium: "O-Methylation of Phenolic Phenethylamine", Chemistry Discourse) Diazomethane: Prep and Use: Warning: Diazomethane is a very dangerous substance (explosive) and must be properly researched before use. Post 288566 (Antoncho: "Diazomethane. Methylations with diazomethane.", Novel Discourse) Post 484470 (Vitus_Verdegast: "Preparation of diazomethane solutions", Novel Discourse) Post 484552 (Rhodium: "Diazald Diazomethane", Novel Discourse) Dimethyloxalate:DMO Mentioned only: Post 503306 (ning: "Try dimethyl oxalate", Novel Discourse) Betaine Post 412790 (Lego: "Betaine for O-methylation of Phenols", Novel Discourse) Trimethylphosphate:TMP https://www.rhodium.ws/chemistry/me3po4.html Post 478120 (Vitus_Verdegast: "To avoid having to make DMS", Methods Discourse) (multiple links on this post) MeOH: (yes, Methanol) Post 421068 (Mountain_Girl: "P-MeO Phenol abstracts 1980-1999 #1", Methods Discourse) (one example is at reflux) NaMeSO₄: Sodium Methylsulfate Post 256342 (Antoncho: "Methylation of hydroquinone w/NaMeSO4: good news!", Novel Discourse) Post 218431 (PolytheneSam: "Re: ArOR, Alternatives to dimethyl sulfate", Novel Discourse) KMeSO₄:Potassium Methylsulfate Post 229389 (PolytheneSam: "Re: ArOR, Alternatives to dimethyl sulfate", Novel Discourse) Phenyltrimethylammonium Chloride Post 443586 (Lego: "O-Methylation with Phenyltrimethylammonium chlorid", Novel Discourse) Random patents about O-Alkylation: Post 221040 (PolytheneSam: "Re: ArOR, Alternatives to dimethyl sulfate", Novel Discourse) Trimethyloxonium Fluoroborate Post 467042 (zealot: "TRIETHYLOXONIUM FLUOBORATE", Novel Discourse) (exotic, but interesting) Gramine (not for the usual phenolic alkylation, this is for tryptamine chemistry) Post 495965 (Nicodem: "The papers mentioned in the above post", Tryptamine Chemistry) Special thanks to Lego for offering help and showing interest in this project. Act quickly or not at all.