Head-to-head poly(2-vinylnaphthalene) was prepared in five steps from 2-naphthylacetic acid. The methyl ester was brominated with N-bromosuccinimide and 2(2-naphthyl)2-bromoacetate treated with a copper/zinc couple, which gave dimethyl 2,3-di(2-naphthyl)succinate in moderate yield. This compound was reduced with lithium aluminum hydride to 2,3-di(2-naphthyl)butanediol-1,4 and the hydroxyl groups replaced by bromine. 2,3-Di(2-naphthyl)-1,4-dibromobutane was subjected to the Yamamoto coupling polycondensation; head-to-head poly(2-vinylnaphthalene) was obtained in relatively low yield and of modest molecular weight.