Liquid-phase reactions of isomeric methylphenols with ozone

Ozonation of isomeric methylphenols in acetic anhydride was studied. Here, acetic anhydride acts simultaneously as solvent and acylating agent. In the presence of a mineral acid methylphenols were converted into methylphenyl acetates during preparation of solutions for ozonation. The major products in the oxidation of isomeric methylphenyl acetates with ozone were aliphatic peroxides (80–90%); oxidation of the methyl group gave rise to the corresponding acetoxybenzyl acetates (7–14%) and acetoxybenzylidene diacetates (3–6%). A probable scheme for the liquid-phase oxidation of methylphenyl acetates with ozone in acetic anhydride was proposed.