Acetyl chloride → 1-((1,1'-Biphenyl)-3-yl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

3-Biphenylmagnesium bromide was prepared according to known procedures from 100 g of 3-bromobiphenyl and 10 g of magnesium turnings in diethyl ether. To the Grignard reagent solution at 4°C was added 40 g of cadmium chloride dihydrate over a 1-hour period. The reaction mixture was heated at reflux for one hour and cooled to 12°C. To the reaction mixture then was added a solution of 32 g of acetyl chloride in diethyl ether over a period of 30 minutes. The reaction mixture was heated at reflux for 30 minutes, allowed to cool to room temperature, and agitated overnight. Additional diethyl ether was added and the reaction mixture again was heated at reflux for one hour. The reaction mixture was cooled and successively treated with 100 ml of saturated aqueous ammonium chloride and 100 ml of water. The reaction mixture was poured over ice, the diethyl ether layer which formed was separated, and the aqueous layer was extracted with diethyl ether. The diethyl ether layer and extracts were combined, washed successively with water until the wash water was neutral to litmus paper, and dried over anhydrous sodium sulfate. The diethyl ether was evaporated and the residue was vacuum distilled to give 29.3 g of 3'-phenylacetophenone, bp 12°C/0.3 mm. The following elemental analysis was obtained:

Provenance & Evidence