(4-tert-Butylcyclohexylidene)acetic acid methyl ester → Methyl 2-(4-tert-butylcyclohexyl)acetate

Participants

Reaction Steps

(4-tert-Butylcyclohexylidene)acetic acid methyl ester (10.78 g, 51.3 mmol) was dissolved in methanol (50 ml). Palladium hydroxide on carbon (1.0 g) was added and the reaction mixture was stirred at room temperature under an atmosphere of hydrogen overnight. The catalyst was then removed by filtration through celite and the filtrate was evaporated in vacuo to a clear oil (9.81 g, 91%). 1H-NMR; δ (CDCl3) (as a mixture of cis-trans isomers), 3.67 (3H, s), 2.38 (1H, d, J=8 Hz), 2.18 (1H, d, 7 Hz), 1.85-1.44 (5H, m), 1.20-0.89 (5H, m) and 0.86 (9H, s).

Provenance & Evidence