Australian Journal of Chemistry p. 1287 - 1291 (1996)
Update date:2022-08-02
Bourke, David G.
Collins, David J.
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).
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(1996)
