Dimethyl Carbonate → 3-Methyl-2-oxo-3-phenyl-cyclohexanecarboxylic acid methyl ester

Participants

Reaction Steps

A mixture of 2-methyl-2-phenylcyclohexanone (4.7 g, 25 mmol) from Preparation 3 above, and sodium hydride (1.1 g of 60% dispersion in mineral oil, 28 mmol) in 15 mL of dimethyl carbonate and 75 mL of benzene, was heated under reflux for 4 h. The mixture was cooled to room temperature and poured into dilute ice-cold aqueous HCl. The organic layer was washed with brine, dried (sodium sulfate) and evaporated to afford 6.36 g of 3-methyl-2-oxo-3-phenyl-cyclohexanecarboxylic acid methyl ester as an oil.

Provenance & Evidence