A classic undergraduate experiment is the Vitamin B1-catalyzed benzoin condensation of benzaldehyde, which introduces students to the concepts of catalysis using N-heterocyclic carbenes in the context of an unfamiliar, umpolung" carbonyl condensation mechanism. The production of benzoin in this way is often part of a longer, four lab period total synthesis of the antiseizure drug phenytoin. The benzoin condensation itself either requires 1.5-2 hours of reflux in ethanol, or 1 week at room temperature. Either of these conditions will necessitate that an entire lab period be dedicated to the benzoin condensation. Our work reported herein dramatically shortens the overall reaction time to 5 minutes in a domestic microwave with no reduction in yield, consequently saving time and energy. Conditions of the reaction and workup are reported, as well as suggestions for incorporating the improvements into the laboratory curriculum.

Green benzoin condensation catalyzed by N-heterocyclic carbenes using a domestic microwave oven

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.