(Active Asperger Archivist)
06-06-04 02:33
No 511704
(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
../rhodium /me3po4.
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.
