Benzaldehyde → 7-Phenyl-6-heptenoic acid

Participants

Reaction Steps

5-Carboxypentyl-triphenylphosphonium bromide (20 g) and benzaldehyde (5.6 g) were suspended in isopropanol (100 ml). To the suspension was added potassium butoxide (10.8 g) in limited amounts at 25° C., then the reaction was allowed to proceed for 2 hours at 70° C. Isopropanol was distilled off under reduced pressure. To the residue was added water (100 ml) to make a solution, which was acidified with hydrochloric acid, followed by extraction with ethyl acetate. The extract was washed with water, dried and concentrated under reduced pressure. The concentrate was subjected to a silica gel column chromatography to afford 7-phenyl-6-heptenoic acid (7.6 g) as a colorless oily product.

Provenance & Evidence