Reactions with thioethoxide ion in N,N-dimethylformamide. III. Regioselective demethylation of 4-(2',7'-Dimethoxy-1'-naphthyl)-2-methylbutan-2-ol

Abstract

Reaction of 2,7-dimethoxy-1-methylnaphthalene with sodium thioethoxide in N,N-dimethylformamide leads to a mixture of approximately equal parts of the isomeric O-monomethyl ethers of 1-methylnaphthalene-2,7-diol, but under the same conditions 4-(2',7'-dimethoxy-1'-naphthyl)-2-methylbutan-2-ol undergoes regioselective demethylation of the more hindered 2'-methoxyl group.