[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[O:5]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[N:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)[CH2:1][CH2:2][CH2:3][CH3:4]A mixture of 7.2 g (0.040 mol) of 4-butoxybenzaldehyde, 4.0 g (0.044 mol) of aniline, 0.10 g of p-toluenesulfonic acid, and 75 mL of toluene was heated at reflux for 16 hr, with continuous azeotropic separation of the water evolved. Upon cooling, the contents of the flask were chromatographed on silica gel using dichloromethane as the eluent to give 7.8 g (77%) of N-(4-butoxylbenzylidene)aniline as a viscous oil. Crystallization from heptane afforded an analytical sample of a white solid.
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