Oxidation of Alkylaromatics

Abstract

Hydroperoxide at α-position to the aromatic ring is the primary oxidation product formed. In all cases monoalkylbenzenes lead to the formation of benzoic acid. Oxidation in the presence of transition metal salts not only accelerate but also selectively decompose the hydroperoxides. Alkyl naphthalenes mainly produce the corresponding naphthalene carboxylic acids. Hock-rearrangement by the influence of strong acids converts the hydroperoxides to hemiacetals. Peresters formed from the hydroperoxides undergo Criegee rearrangement easily. Alkali metals accelerate the oxidation while CO2 as co-oxidant enhances the selectivity. Microwave conditions give improved yields of the oxidation products.