[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[CH:1](=[N:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Benzaldehyde (0.20 mole) is treated with aniline (0.20 mole) with vigorous stirring in a 1 l. Erlenmeyer Flask. After 15 mins., 33 cc of 95% ethanol is added and the reaction mixture is stirred vigorously for an additional 5 minutes. The reaction mixture is left standing at room temperature for 10 min.; then it is placed in an ice-bath for 0.5 hrs. The crystals which form are collected, washed with 95% ethanol and air-dried. Recrystallization from 85% ethanol gives N-Benzylideneaniline. m.p. 50°-51.5° C.
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