A convenient synthesis of 1-aryl-2-propanone precursors of α-methyldopa

Article abstract of DOI:10.1055/s-1992-26345

A simple two-step approach to 1-(3,4-dimethoxyphenyl)- and 1-[3,4-(methylenedioxy)phenyl]-2-propanone (4a and 4b), useful intermediates for α-methyldopa, is described. It is based on the epoxidation of the widely available methyleugenol (1-allyl-3,4-dimethoxybenzene, 1a) and safrole [1-allyl-3,4-(methylenedioxy)benzene, 1b] with hydrogen peroxide catalyzed by tungsten peroxo complex 2a under two-phase conditions, followed by isomerization of the intermediate epoxides 3a and 3b by lithium iodide.