Dearomatisation of 2-naphthol by oxidative nucleophilic substitution: an efficient two-step process

Abstract

An efficient synthesis of 1,1-dimethoxynaphthalen-2(1H)-one (13) has been achieved. Oxidation of 2-naphthol with bis-p-nitrobenzoyl peroxide gave the known derivative (5). Methylation with diazomethane and hydrolysis afforded 1-methoxy-2-naphthol which was oxidised in methanol to the enone (13) in high yield. The synthesis could also be carried out with benzoyl peroxide, but with lower yields.