Azeotropic Preparation of a C-Phenyl N-Aryl Imine: An Introductory Undergraduate Organic Chemistry Laboratory Experiment

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• 作者：Lee J. Silverberg ; David J. Coyle ; Kevin C. Cannon ; Robert T. Mathers ; Jeffrey A. Richards ; John Tierney
• 刊名：Journal of Chemical Education
• 出版年：2016
• 出版时间：May 10, 2016
• 年：2016
• 卷：93
• 期：5
• 页码：941-944
• 全文大小：217K
• 年卷期：0
• ISSN：1938-1328

文摘

Imines are important in biological chemistry and as intermediates in organic synthesis. An experiment for introductory undergraduate organic chemistry is presented in which benzaldehyde was condensed with p-methoxyaniline in toluene to give 4-methoxy-N-(phenylmethylene)benzenamine. Water was removed by azeotropic distillation using a Dean–Stark trap. The reaction was readily performed in one 3 h laboratory period, gave a crystalline product, and was easily followed visually by the amount of water collected. It demonstrated important concepts from second-year undergraduate organic chemistry, including equilibrium processes, condensation reactions, and imine formation. The experiment also gave students exposure to important laboratory techniques including azeotropic distillation, use of a water trap, and mixed-solvent recrystallization.