Hydrochloric Acid → 4-Benzoylbiphenyl

Participants

Reaction Steps

In an oven-dried flask placed under a nitrogen atmosphere biphenyl (50 g) was stirred in dichloromethane (450 mL). The flask was placed in an ice bath and to it was added benzoyl chloride (46 mL) via addition funnel slowly over 20 minutes. To that mixture was added anhydrous aluminum chloride (51 g) via solid addition funnel, slowly over 10 minutes. After the aluminum chloride addition was complete the reaction mixture allowed to warm to room temperature and to stir for 16 hours. The reaction mixture was slowly poured into a beaker containing ice and a 10% aqueous solution of hydrochloric acid (600 mL) while stirring vigorously. A separatory funnel was used to separate the organic and aqueous layers. The recovered organic layer was then washed with water (2×500 mL), washed with a saturated aqueous solution of sodium chloride (500 mL), dried over sodium sulfate and concentrated by rotary evaporation. The resulting solid was slurried in a 25% v/v mixture of ethyl acetate in hexanes. The solid was collected by vacuum filtration, and then washed with cold diethyl ether (2×200 mL) to yield 57 g of [1,1′-biphenyl]-4-yl(phenyl)methanone.

Provenance & Evidence