preparation | A ml Four-necked flask was equipped with a mechanical stirrer, a reflux condenser, a thermometer and an addition funnel. The flask was cooled with an ice-water bath as needed. 86 grams of deionized water, 9.8 grams (0.16 moles) of acetic acid, and 216 grams (3.0 moles) of butyraldehyde were added to the flask. While cooling and stirring, 60g (0.64 mol) of aniline were added over a period of 35 minutes while maintaining the reaction temperature at 20°C. The reaction mixture was stirred at 25°C or below for one hour. The reaction mixture was then heated to 75°C and incubated for two hours. Finally, the reaction mixture was heated to reflux (-90°C) and incubated for five hours. The reaction mixture was cooled and the layers were separated. The upper organic layer was distilled under reduced pressure through a 14 "packed column. The fraction taken at an overhead temperature of 140-143°C and a pressure of 5mm Hg weighed 104 grams and was analyzed to contain 73% DHP for an overall yield of 46%. |