1,3-Benzodioxole-2-spirocyclohexadien-4′-one and some of its derivatives

Abstract

The synthesis of 2,4′-dihydroxydiphenyl ether, and of some of its homologues, and of some of the analogous dihydroxy-derivatives of naphthyl phenyl ethers is described. They were obtained by demethylating the corresponding methoxy-compounds. Oxidation of 2,4′-dihydroxydiphenyl ether gave a low yield of 1,3-benzodioxole-2-spirocyclohexadien-4′-one; five other examples of this type of conversion were observed. In particular, 4-(2-hydroxyphenoxy)-1-naphthol gave 1,3-benzodioxole-2-spiro-1′-naphthalen-4′-one in quantitative yield.