Benzyl Alcohol → Benzyl 2-oxocyclopentane-1-carboxylate

Participants

Reaction Steps

In a 4-liter flask fitted with a Dean-Stark apparatus and a condenser, methyl 2-oxo-cyclopentanecarboxylate (380 mL; 3 mol), benzyl alcohol (342 mL; 3.3 mol; 1.1 eq.) and DMAP (18.3 g; 0.15 mol; 0.05 eq.) are dissolved in 1800 mL of cyclohexane. The reaction mixture is stirred for 48 hours at reflux (temperature of the mixture: 90° C.) and the methanol formed is distilled off. After cooling, the reaction mixture is concentrated and taken up in 1500 mL of dichloromethane. The organic phase is washed with 1N hydrochloric acid, with water, and then with saturated sodium chloride solution. It is then dried, filtered and then evaporated.

Provenance & Evidence