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

• Lee J. Silverberg ^[1] ; David J. Coyle ^[1] ; Kevin C. Cannon ^[1] ; Robert T. Mathers ^[1] ; Jeffrey A. Richards ^[1] ; John Tierney ^[1]
  1. [1] Pennsylvania State University

     Pennsylvania State University

     Borough of State College, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 93, Nº 5, 2016, págs. 941-944
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • 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.