Benzyl Alcohol → Benzyl 2-cyclopentylacetate

Participants

Reaction Steps

p-Toluene sulfonic acid monohydrate (1.48 g, 7.82 mmol) was added to a solution of cyclopentylacetic acid (10.0 g, 78.2 mmol) and benzyl alcohol (8.42 g, 78.2 mmol) in toluene (100 ml) at room temperature, a Dean-Stark water separator was mounted, and the mixture was refluxed for 4 hr. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure, the residue was dissolved in ether, the solution was washed with saturated sodium bicarbonate and saturated brine and was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=97:3) to give the title compound as a light yellow oil (12.0 g, yield 70%).

Provenance & Evidence