Fries Rearrangement Accelerated by Microwave Radiation in the Undergraduate Organic Laboratory

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Abstract

Herein we present an opportunity for undergraduate students to carry out a reaction using microwave radiation. The rapid rate of reaction prevents student boredom and inactivity. The rate increase appears to be due primarily to rapid attainment of high reaction temperatures. However, the possibility of an additional modest acceleration in rate due to some effect specific to the microwave wavelengths employed has not been completely excluded. We have found that the Fries rearrangement of aryl esters to ortho- and para-hydroxy acetophenones can be carried out in dry open media in ordinary glassware using a commercial microwave oven. The Fries rearrangement normally requires a Lewis acid and long reflux times or photochemical conditions.

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