Methods of O-Dealkylation

[Aurelius]

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 (missing)

(Lego: "Demethylation with AlCl3-NaI w/o solvent", Methods Discourse)
AlCl₃ / Pyridine

https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html#ali3

AlBr₃ / Nitrobenzene

https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html#ali3

LiCl/DMF

Post 444300 (missing)

(Lego: "Dealkylation with LiCl/DMF", Methods Discourse)
Li Diphenylphosphinate

https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html#ali3

Ionic Liquid Reagents:
Chloroaluminate Ionic liquid Reagents

Post 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/H₃PO₄
    

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:
SIBX

Post 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-HCl

https://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)