Thionyl Chloride → HCID 9992887, compound

Participants

Reaction Steps

To a solution of 2,2-bis(p-tolyl)-4-pentenoic acid (8.17 g) in N,N-dimethylformamide (1.0 ml) and methylene chloride (45 ml) was added thionyl chloride (3.2 ml), and the solution was stirred at room temperature for 1 day. The solution was evaporated in vacuo and the residue was dissolved in methylene chloride (50 ml). The solution was added dropwise to a suspension of aluminum chloride (4.66 g) in methylene chloride (50 ml) with dry ice-acetone bath cooling under nitrogen atmosphere, and the resulting mixture was stirred at room temperature overnight. The mixture was poured into cooled 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, water, 1N sodium hydroxide, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate (10:1~5:1) as an eluent to give 5,5-bis(p-tolyl)-2-cyclopenten-1-one (2.30 g).

Provenance & Evidence