3-(2-Chlorophenyl)propanoic acid → 4-chloro-2,3-dihydro-1H-inden-1-one

Participants

Reaction Steps

A mixture of 200 ml of polyphosphoric acid and 23.6 g (128 mmol) of 3-(2-chlorophenyl)-propanoic acid was heated on the steam bath for six hours. The mixture was allowed to cool, diluted with 500 ml of water, and the resulting solid collected. The solid was partitioned between ether and saturated sodium bicarbonate, the ether layer was separated, dried (MgSO4), and concentrated to a solid. The solid was crystallized from ether/hexane to give 7.8 g (37%) of 4-chloro-2,3-dihydro-1H-inden-1-one; mp 89°-92°.

Provenance & Evidence