Benzene → HCID 19981496, compound

Participants

Reaction Steps

A mixture of 2,2-diphenyl-4-pentenenitrile (2.33 g), 3.0M ethylmagnesium bromide in ether (10 ml), and benzene (30 ml) was heated at reflux for 3 hours, with stirring. After cooling to room temperature, the crude intermediate was stirred with 1N hydrochloric acid for 3 hours. The hydrolysate was partitioned between water and ethyl acetate (3×). The combined extracts were washed with water and brine, dried (MgSO4), and rotary evaporated to give a crude material which was flash-chromatographed over silica gel. Elution with hexane/ethyl acetate (5:1) yielded 1.0 g of 4,4-diphenyl-6-hepten-3-one, as a colorless oil.

Provenance & Evidence