Dimethylformamide → 3-(1-Cyano-1-methylethyl)benzoyl chloride

Participants

Reaction Steps

3-(1-Cyano-1-methylethyl)benzoic acid (20.0 g, 105 mmol) was dissolved in tetrahydrofuran (105 mL), and oxalyl chloride (10.8 mL, 126 mmol) and N,N-dimethylformamide (20 μL) were added. The reaction mixture was stirred at room temperature for 1 hr, and the solvent was evaporated under reduced pressure to give 3-(1-cyano-1-methylethyl)benzoyl chloride. To a solution of 3-aminophenol (11.4 g, 105 mmol) in tetrahydrofuran (200 mL) was added a suspension of sodium hydrogen carbonate (26.5 g, 315 mmol) in water (315 mL), and the mixture was vigorously stirred at room temperature. A solution of 3-(1-cyano-1-methylethyl)benzoyl chloride in tetrahydrofuran (105 mL) produced above was added dropwise, and the mixture was stirred at room temperature for 16 hr. Ethyl acetate (300 mL) was added to the reaction mixture, and the aqueous layer was separated. The organic layer was washed with saturated brine (300 mL) and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained solid was washed with a mixed solvent (1:1) of diisopropyl ether and n-hexane to give the title compound (27.0 g, 92%) as a white powder.

Provenance & Evidence