The condensation of acetylenes with deoxyanisoin

Abstract

Although deoxyanisoin underwent fission on attempted reaction with sodium or lithium acetylide in liquid ammonia, it condensed normally with 1-hexyne and propyne via the Grignard reagent, the intermediate aoetylenic carbinols dehydrating on distillation. The reaction of acetylenedimagnesium bromide and deoxyanisoin at room temperature afforded the stable 1,2-di-(p-methoxyphenyl)but-3-yn-2-ol, whereas the same reagents under more vigorous conditions resulted in cyclization to 2-methoxy-6-p-methoxyphenylnaphthalene, synthesized from anisil or deoxyanisoin by a Reformatsky reaction via the tetralone.