Dakin Oxidation of o-Hydroxyacetophenone and some Benzophenones: Rate Enhancement and Mechanistic Aspects

Abstract

A synthetic aqueous alkaline hydrogen peroxide solution, made up to approximate the concentrations of caustic and hydrogen peroxide expected from water washing of aerated sodium amalgam, readily oxidized o-hydroxyacetophenone to catechol. The relevance of a proposed ester intermediate of this reaction is discussed, and also the possibility of using o-hydroxybenzophenone (originating from phenylben-zoate) as a substrate is briefly considered.