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 (missing)
(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 TosylatePost 417550
(Antoncho: "Methyl tosylate: _finally_ , OTC!!!", Novel Discourse)Post 466982 (missing)
(psyloxy: "practical alkyl tosylate synth - new approaches", Novel Discourse)Post 505605 (missing)
(psyloxy: "the important parts", Chemistry Discourse)Post 461039
(psyloxy: "Ethyl toluenesulfonate from TsOH/ CH2(COOEt)2, 50%", Chemistry Discourse)Dimethylsulfate: DMSExamples 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: DMCPost 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:DMOMentioned only:
Post 503306
(ning: "Try dimethyl oxalate", Novel Discourse)BetainePost 412790
(Lego: "Betaine for O-methylation of Phenols", Novel Discourse)Trimethylphosphate:TMPhttps://www.thevespiary.org/rhodium/Rhodium/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 MethylsulfatePost 256342
(Antoncho: "Methylation of hydroquinone w/NaMeSO4: good news!", Novel Discourse)Post 218431
(PolytheneSam: "Re: ArOR, Alternatives to dimethyl sulfate", Novel Discourse)KMeSO4:Potassium MethylsulfatePost 229389
(PolytheneSam: "Re: ArOR, Alternatives to dimethyl sulfate", Novel Discourse)Phenyltrimethylammonium ChloridePost 443586 (missing)
(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 FluoroboratePost 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.
