Syntheses of Benzenediols by the Reactions of Phenol with Peroxides, Obtained from Ketones and Hydrogen Peroxide

Abstract

The acid-catalyzed reaction of phenol with various organic peroxides was investigated to obtain such benzenediols as catechol and hydroquinone. Among the tested peroxides, “ketone peroxides”, obtained from ketones and hydrogen per-oxide, were found to give benzenediols in high yield. In the reactions, when catalysts such as sulfuric acid, perchloric acid, sulfonic acid, and sulfates were used, the molar ratio of catechol to hydroquinone formed was about 3 : 2, and when catalyst such as a mixture of clay and phosphoric acid was used, this ratio was 1 : 1. The reaction of substituted phenols with ketone peroxides was also investigated. The reaction was regarded as an electrophilic substitution one on the basis of the composi-tion of products and the quantum chemical calculation.