Synthesis and Some Reactions of 1-(Trimethoxymethyl)cyclohexene

Abstract

1-( Trimethoxymethyl ) cyclohexene (11) was synthesized in three steps from N-methyl-N-phenylcyclohex-1-ene-1-carboxamide (8). Reaction of the α,β -unsaturated ortho ester (11) with sodium hydride and N- methylaniline gave a 1:1 mixture of methyl cyclohex-1-ene-1-carboxylate (15) and N,N- dimethylaniline . Treatment of (11) with 3-methoxyphenol gave 1-[ dimethoxy (3'-methoxyphenoxy)methyl] cyclohexene (10) which underwent thermolysis at 250° to give 1,3-dimethoxybenzene (16) and methyl cyclohex-1-ene-1-carboxylate (15).