Hydrochloric Acid → 3-Benzyloxy-5-hydroxy-N,N-dimethylbenzamide

Participants

Reaction Steps

3-Acetoxy-5-benzyloxybenzoic acid (1.0 g) was suspended in dichloromethane (12 mL), oxalyl chloride (0.49 g), N,N-dimethylformamide (0.01 mL), tetrahydrofuran was added sequentially, and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and then dichloromethane was added to the residue. Dimethylamine hydrochloride (0.28 g) and pyridine (0.1 mL) were added to the reaction mixture and stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained was dissolved in tetrahydrofuran (15 mL). Sodium methoxide-methanol solution (5.2 mol/L, 1.02 mL) was added to the reaction mixture and stirred at room temperature for 30 minutes. One mol/L hydrochloric acid was added to the reaction mixture and the whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by column chromatography on silica gel (eluent: ethylacetate/hexane=1/1) to give the title compound (0.67 g).

Provenance & Evidence