NAPHTHALENE DERIVATIVES FROM SUBSTITUTED γ-PHENYLCROTONIC ESTERS

Publisher Website
Google Scholar
Abstract
The product of the condensation of phenylacetone with ethyl malonate, i.e., ethyl α-carbethoxy-β-methyl-γ-phenyl-butenoate, when saponified, gives rise to 3-methyl-1-hydroxy-2-naphthoic acid. This can be decarboxylated to a naphthol identical with 3-methyl-1-naphthol prepared by a series of reactions from β-methyl-naphthalene. The synthetic naphthol, in the Kolbe synthesis, yields 3-methyl-1-hydroxy-2-naphthoic acid, identical with the acid produced when the condensation ester is saponified. The condensation of phenylacetone with ethyl cyanoacetate gives rise to an unsaturated ester which does not cyclize spontaneously, but only when heated in glycerol, to a phenolic compound, probably 1-hydroxy-3-methyl-2-naphthoic nitrile.

This publication has 0 references indexed in Scilit: