Methods of O-Dealkylation:Using:
MeMgIPost 507775
(Rhodium: "Schöpf: MeMgI Demethylation of Eugenol", Chemistry Discourse)General Lewis Acids:AlI3Post 422757
(GC_MS: "Aluminium iodide in ether cleavage", Methods Discourse)Post 68536
(startinout: "Success, finally", Novel Discourse)AlCl3-NaI / no solventPost 444270 (missing)
(Lego: "Demethylation with AlCl3-NaI w/o solvent", Methods Discourse)AlCl3 / Pyridinehttps://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html#ali3
AlBr3 / Nitrobenzenehttps://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html#ali3
LiCl/DMFPost 444300 (missing)
(Lego: "Dealkylation with LiCl/DMF", Methods Discourse)Li Diphenylphosphinatehttps://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html#ali3
Ionic Liquid Reagents:Chloroaluminate Ionic liquid ReagentsPost 445940 (missing)
(Lego: "Chloroaluminate Ionic Liquid Reagents", Methods Discourse)[BMIM]-[X]Post 505891 (missing)
(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/H
3PO
4 Post 504369 (missing)
(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:SIBXPost 451672
(Rhodium: "Novel Oxidative Demethylation of Eugenol", Novel Discourse) IBX Synth: Post 219075 (missing)
(foxy2: "2-Iodoxybenzoic Acid (IBX) Synthesis", Chemistry Discourse) (from:)
2-Iodobenzoic Acid Post 219077 (missing)
(foxy2: "2-Iodobenzoic Acid Synthesis", Chemistry Discourse)Microwave Methdods:Pyridine-HClhttps://www.thevespiary.org/rhodium/Rhodium/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)