Session S55a (Monday, 5:15pm, Willaman Gateway)

P338: Imine condensation: Green chemistry experiment for sophomore organic chemistry laboratory

Natalia Blank, David Blank (Norwich University, USA)

Imine condensation reactions are discussed in great detail in classic organic chemistry textbooks. Interestingly, there are very few laboratory experiments suitable for a sophomore organic chemistry course that demonstrate this reaction. The most likely reason is the fact that the traditional synthetic imine preparations involve use of organic solvents and reagents with unpleasant smells, harsh reaction conditions and lengthy separation and purification. Recently new methods of imine condensation have been reported which are more environmentally friendly and much shorter and therefore could be adapted to a 3-hour laboratory period. We are reporting such an experiment that involves mini-scale synthesis of p-phenyl-benzylideneaniline from aniline and p-phenylbenzaldehyde in water. The product imine is purified by re-crystallization from ethanol and characterized by MP, IR and NMR spectroscopy. This experiment is an easy and inexpensive way to illustrate the imine condensation as well as teach students about atom economy and uses of green solvents.


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