Autoxidation of 3,4-dihydro-1-methylnaphthalen-2(1H)-one

Abstract

3,4-Dihydro-1-methylnaphthalen-2(1H)-one (1) is found to undergo autoxidation giving at least three distinct crystalline products, namely. 3-(2-acetylphenyl)propionic acid (5), 1,1′-bi-[3,4-dihydro-1-methylnaphthalen-2(1H)-one](7), and 3,4-dihydro-1-hydroxy-1-methylnaphthalen-2(1H)-one (6). A new synthesis of the ketone (1) is described using a modified Curtius reaction with 3,4-dihydro-1-methyl-2-naphthoic acid (8) which excludes the use of any oxidising agent.