The purpose of this research project was to develop an undergraduate organic laboratory experiment to provide a demonstrable example of the Pinacol rearrangement and to provide practical spectroscopic and spectrometric instrumental experience. The chemical synthesized in this experiment is Phenytoin, an antiepileptic drug that was first synthesized in 1908 by the Biltz synthesis. This synthesis involves base catalyzed addition of Urea to benzil followed by Pinacol rearrangement to form Phenytoin. This is an ideal synthesis for demonstrating the Pinacol rearrangement at the undergraduate level, since the starting materials are readily accessible, the synthesis can be achieved and product isolated within a three to four hour time frame, and the product is easily characterized using FTIR, H-NMR, LCMS and DART-MS.

Synthesis and spectroscopic/spectrometric analysis of the pharmaceutical phenytoin demonstrating the Pinacol rearrangement

2019 Spring National Meeting

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