Acetic Acid → 3-Chloro-1,1-diphenylpropene

Participants

Reaction Conditions

Reaction Steps

A 300-ml reaction flask was charged with 54.13 g (0.3 mol) of 1,1-diphenylethylene (9a), 108.26 g of acetic acid and 13.51 g (0.45 mol) of paraformaldehyde, and 13.67 g (0.375 mol) of hydrogen chloride was blown in with stirring at 30° C. for 3.5 hours. The reaction temperature was kept at 30° C. by cooling because of weak heat development. The blowing-in of hydrogen chloride was stopped, and the solution was stirred at the same temperature for 2 hours, followed by standing overnight. The reaction solution was poured into 200 ml of water, followed by extraction with 200 ml of toluene. The resulting product was washed with water, washed with 2% soda ash, washed with water, dried over magnesium sulfate, and concentrated to obtain 68.42 g of a crude chloride. It was distilled in a Claisen flask equipped with a vigreux to obtain 57.51 g.

Provenance & Evidence