3,5-Dimethylcyclohex-2-en-1-one → AG-G-83630

Participants

Reaction Steps

A solution of 3,5-dimethyl-2-cyclohexenone (2.0 g, 16.1 mmol) in 2-propanol (32 ml) was hydrogenated over 5% palladium on charcoal (200 mg) at room temperature and 103 kPa (14.7 psi) for 4 hours, then diluted with 1:1 hexane:ether (150 ml) and filtered using a filter aid. The filtrate was evaporated under reduced pressure to provided the substantially stereochemically pure title compound (1.56 g) as a yellow oil. 13C NMR spectroscopy revealed a cis:trans ratio of 150:3.

Provenance & Evidence