105580-41-4

79-37-8

586-89-0

105580-41-4

(1) 4-Acetylbenzoic acid (100 g) was suspended in 500 mL of dichloromethane. To this suspension 64 mL of oxalyl chloride and 4.7 mL of N,N-dimethylformamide were slowly added at room temperature and the mixture was stirred for 2 hours at room temperature. Upon completion of the reaction, the reaction solution was concentrated under reduced pressure and the residue was dissolved with 250 mL of chloroform and 175 mL of tert-butanol. Subsequently, 156 mL of pyridine was slowly added dropwise to this solution under cooling in an ice bath, keeping the reaction temperature at about 12°C. After the dropwise addition was completed, the reaction mixture was stirred at room temperature for 30 minutes and subsequently concentrated under reduced pressure. The concentrated residue was dissolved in toluene and the organic layer was washed sequentially with 2M hydrochloric acid, saturated aqueous sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Hexane was added to the concentrated residue and the mixture was stirred under cooling in an ice bath. The precipitated crystals were collected by filtration, washed with cold hexane and dried under vacuum to give tert-butyl 4-acetylbenzoate as a white solid (96.82 g, yield 69%). The melting point of the product was 59-60°C.