Cleavage or Acetyl-de-alkylation of 4-Methoxybenzyl (MPM) Ethers Using Acetic Acid

1 April 1994

journal article
research article
Published by Taylor & Francis in Synthetic Communications

Vol. 24 (8) , 1151-1155
https://doi.org/10.1080/00397919408011711

Abstract

Aryl (4-methoxyphenyl)methyl (MPM) ethers are cleaved by heating with acetic acid for a few hours at 90°C, producing the corresponding phenols and (4-methoxyphenyl)methyl acetate. Under the same conditions alkyl MPM ethers are transformed directly into the corresponding alkyl acetates.

Keywords

This publication has 11 references indexed in Scilit:

Tin(II) Bromide - Acetyl Bromide: A Mild and Efficient Reagent for Direct Conversion of Alcohol Benzyl Ethers into Acetates
Synlett, 1993
A new reagent for the removal of the 4-methoxybenzyl ether: application to the synthesis of unusual macrocyclic and bolaform phosphatidylcholines.
The Journal of Organic Chemistry, 1992
N-nitrosohydroxylamines I. Acetolysis and acid-catalyzed hydrolysis of N,O-dibenzyl-N-nitrosohydroxylamines. Reaction with potassium t-butoxide
Tetrahedron, 1992
Conjugate addition to 3-(ptolylsulphinyl)chromone: a route to 2-substituted chromones and chiral substituted chroman-4-ones
Tetrahedron, 1990
Total synthesis of geodiamolide A, a novel cyclodepsipeptide of marine origin
The Journal of Organic Chemistry, 1989
3-Methoxybenzyl (3-MPM) and 3,5-dimethoxybenzyl (3,5-DMPM) protecting groups for the hydroxy function less readily removable than 4-methoxybenzyl (MPM) and 3,4-dimethoxybenzyl (DMPM) protecting groups by DDQ oxidation.
CHEMICAL & PHARMACEUTICAL BULLETIN, 1988
On the selectivity of deprotection of benzyl, mpm (4-methoxybenzyl) and dmpm (3,4-dimethoxybenzyl) protecting groups for hydroxy functions
Tetrahedron, 1986
NMR Studies of Lignins. 1. Signals Due to Protons in Formyl Groups.
Acta Chemica Scandinavica, 1977
Ferric chloride in acetic anhydide. Mild and versatile reagent for the cleavage of ethers
The Journal of Organic Chemistry, 1974
Substituent Effects in Pyrolysis. V.^1,2 A p-σ⁺ Correlation in the Pyrolysis of 1-Arylethyl Acetates
Journal of the American Chemical Society, 1962