title: Additional Nucleophile-Free FeCl3-Catalyzed Green Deprotection of 2,4-Dimethoxyphenylmethyl-Protected Alcohols and Carboxylic Acids.
abstract: The deprotection of the methoxyphenylmethyl (MPM) ether and ester derivatives can be generally achieved by the combinatorial use of a catalytic Lewis acid and stoichiometric nucleophile. The deprotections of 2,4-dimethoxyphenylmethyl (DMPM)-protected alcohols and carboxylic acids were found to be effectively catalyzed by iron(III) chloride without any additional nucleophile to form the deprotected mother alcohols and carboxylic acids in excellent yields. Since the present deprotection proceeds via the self-assembling mechanism of the 2,4-DMPM protective group itself to give the hardly-soluble resorcinarene derivative as a precipitate, the rigorous purification process by silica-gel column chromatography was unnecessary and the sufficiently-pure alcohols and carboxylic acids were easily obtained in satisfactory yields after simple filtration.
authors.affiliation: Gifu Pharmaceutical University.
authors.forename: Yoshinari
authors.initials: Y
authors.lastname: Sawama
authors.forename: Masahiro
authors.initials: M
authors.lastname: Masuda
authors.forename: Akie
authors.initials: A
authors.lastname: Honda
authors.forename: Hiroki
authors.initials: H
authors.lastname: Yokoyama
authors.forename: Kwihwan
authors.initials: K
authors.lastname: Park
authors.forename: Naoki
authors.initials: N
authors.lastname: Yasukawa
authors.forename: Yasunari
authors.initials: Y
authors.lastname: Monguchi
authors.forename: Hironao
authors.initials: H
authors.lastname: Sajiki
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry*; D055772:Green Chemistry Technology; D015394:Molecular Structure
chemical_list: D000438:Alcohols; D002264:Carboxylic Acids; D002712:Chlorides; D005290:Ferric Compounds; C024555:ferric chloride