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Digest: Methods of O-Dealkylation Please login to post

Aurelius
(Active Asperger Archivist)
06-07-04 05:18
No 511901
      Methods of O-Dealkylation
(Rated as: excellent)

Methods of O-Dealkylation:

Using:
MeMgI
Post 507775 (Rhodium: "Schöpf: MeMgI Demethylation of Eugenol", Chemistry Discourse)

General Lewis Acids:
AlI₃
Post 422757 (GC_MS: "Aluminium iodide in ether cleavage", Methods Discourse)
Post 68536 (startinout: "Success, finally", Novel Discourse)
AlCl₃-NaI / no solvent
Post 444270 (Lego: "Demethylation with AlCl3-NaI w/o solvent", Methods Discourse)
AlCl₃ / Pyridine
https://www.rhodium.ws/chemistry/methylenation.html#ali3
AlBr₃ / Nitrobenzene
https://www.rhodium.ws/chemistry/methylenation.html#ali3
LiCl/DMF
Post 444300 (Lego: "Dealkylation with LiCl/DMF", Methods Discourse)
Li Diphenylphosphinate
https://www.rhodium.ws/chemistry/methylenation.html#ali3
Ionic Liquid Reagents:
Chloroaluminate Ionic liquid Reagents
Post 445940 (Lego: "Chloroaluminate Ionic Liquid Reagents", Methods Discourse)
[BMIM]-[X]
Post 505891 (Lego: "Ether cleavage with ionic liquids", Methods Discourse)

Strong Acids:
HI or equivalent:
   Post 467602 (SPISSHAK: "here are the ref's more to come.", Chemistry Discourse)
   KI/H₃PO₄
   Post 504369 (Lego: "Cleavage of ethers with KI/95% H3PO4", Methods Discourse)
HBr or equivalent:
   Anhydrous HBr
   Post 466086 (Rhodium: "Anhydrous Gaseous Hydrogen Bromide", Methods Discourse)

Oxidative Approaches:
SIBX
Post 451672 (Rhodium: "Novel Oxidative Demethylation of Eugenol", Novel Discourse)
   IBX Synth:
   Post 219075 (foxy2: "2-Iodoxybenzoic Acid (IBX) Synthesis", Chemistry Discourse)
(from:)
   2-Iodobenzoic Acid
   Post 219077 (foxy2: "2-Iodobenzoic Acid Synthesis", Chemistry Discourse)

Microwave Methdods:
Pyridine-HCl
https://www.rhodium.ws/chemistry/methylenation.html#ali3
   Triethylamine lowers yield to ~60%
   See: Post 498486 (9873468096: "Vanillin Demethylation with Pyridine and AlCl31", Newbee Forum)

Wanted References: (please post in approporiate place and then pm me)
Post 467602 (SPISSHAK: "here are the ref's more to come.", Chemistry Discourse)
Post 497390 (merbst: "Lots of references about 3-O-demethylation", Chemistry Discourse)
Post 497391 (merbst: "Lots of references about 3-O-demethylation Part 2", Chemistry Discourse)

Act quickly or not at all.

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		Aurelius (Active Asperger Archivist) 06-07-04 05:18 No 511901				Methods of O-Dealkylation (Rated as: excellent)
						Methods of O-Dealkylation: Using: MeMgI Post 507775 (Rhodium: "Schöpf: MeMgI Demethylation of Eugenol", Chemistry Discourse) General Lewis Acids: AlI₃ Post 422757 (GC_MS: "Aluminium iodide in ether cleavage", Methods Discourse) Post 68536 (startinout: "Success, finally", Novel Discourse) AlCl₃-NaI / no solvent Post 444270 (Lego: "Demethylation with AlCl3-NaI w/o solvent", Methods Discourse) AlCl₃ / Pyridine https://www.rhodium.ws/chemistry/methylenation.html#ali3 AlBr₃ / Nitrobenzene https://www.rhodium.ws/chemistry/methylenation.html#ali3 LiCl/DMF Post 444300 (Lego: "Dealkylation with LiCl/DMF", Methods Discourse) Li Diphenylphosphinate https://www.rhodium.ws/chemistry/methylenation.html#ali3 Ionic Liquid Reagents: Chloroaluminate Ionic liquid Reagents Post 445940 (Lego: "Chloroaluminate Ionic Liquid Reagents", Methods Discourse) [BMIM]-[X] Post 505891 (Lego: "Ether cleavage with ionic liquids", Methods Discourse) Strong Acids: HI or equivalent: Post 467602 (SPISSHAK: "here are the ref's more to come.", Chemistry Discourse) KI/H₃PO₄ Post 504369 (Lego: "Cleavage of ethers with KI/95% H3PO4", Methods Discourse) HBr or equivalent: Anhydrous HBr Post 466086 (Rhodium: "Anhydrous Gaseous Hydrogen Bromide", Methods Discourse) Oxidative Approaches: SIBX Post 451672 (Rhodium: "Novel Oxidative Demethylation of Eugenol", Novel Discourse) IBX Synth: Post 219075 (foxy2: "2-Iodoxybenzoic Acid (IBX) Synthesis", Chemistry Discourse) (from:) 2-Iodobenzoic Acid Post 219077 (foxy2: "2-Iodobenzoic Acid Synthesis", Chemistry Discourse) Microwave Methdods: Pyridine-HCl https://www.rhodium.ws/chemistry/methylenation.html#ali3 Triethylamine lowers yield to ~60% See: Post 498486 (9873468096: "Vanillin Demethylation with Pyridine and AlCl31", Newbee Forum) Wanted References: (please post in approporiate place and then pm me) Post 467602 (SPISSHAK: "here are the ref's more to come.", Chemistry Discourse) Post 497390 (merbst: "Lots of references about 3-O-demethylation", Chemistry Discourse) Post 497391 (merbst: "Lots of references about 3-O-demethylation Part 2", Chemistry Discourse) Act quickly or not at all.