Preparation | Suspend 21.4g(400 mmol) ammonium chloride in 375 ml toluene and cool the suspension to 0°C. Drop 200 ml of 2M trimethylaluminum hexane solution and stir the mixture at room temperature until the escape of the gas has stopped. 29.44g(200mmol) of 2-ethoxybenzonitrile was added, and then the reaction mixture was stirred overnight at 80°C (bath). The cooled reaction mixture was added to a suspension of 100g silica gel and 950ml chloroform under ice cold, and the mixture was stirred at room temperature for 30 minutes. The mixture was pumped out and the filter residue was washed with the same amount of methanol. Evaporate the mother liquor, stir the resulting residue with a mixture of dichloromethane and methanol (9:1), filter the solids, and evaporate the mother liquor. 30.4g(76%) colorless solid was obtained. |