4-(Benzyloxy)-N,N-dimethylphenylacetamide

6547-53-1

506-59-2

919475-15-3

In the presence of a catalytic amount of N,N-dimethylformamide (one drop), 4-benzyloxyphenylacetic acid (100 g, 0.41 mol) was reacted with thionyl chloride (45 ml, 0.62 mol) in refluxing dichloromethane for 6 hours to produce the corresponding chloride. Subsequently, the chloride solution was slowly added to a well-stirred mixture of dimethylamine hydrochloride (101 g, 1.24 mol) and triethylamine (174 ml, 1.24 mol) in dichloromethane while controlling the temperature of the reaction to be below 5 °C. After the addition was completed, stirring of the reaction mixture was continued for 1 hour at 5-10°C. After completion of the reaction, the reaction was quenched by addition of water (1000 ml) and the organic layer was separated. The aqueous layer was extracted with dichloromethane (3 x 500 ml) and after combining all the organic layers, it was washed with water (2 x 500 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. Hexane (700 ml) was added to the crude product and stirred at 25-30 °C for 1 h to promote crystallization. The solid was collected by filtration to afford 2-[4-(benzyloxy)phenyl]-N,N-dimethylacetamide (III) as an off-white solid. The structure of the product was confirmed by 1H-NMR. The weight of the product was 100 g and the molar yield was 90%.