Development of a One-Pot Allylation and Claisen Rearrangement of Acetaminophen by Applying Microwave Radiation

Poster Presentations

The Claisen rearrangement is a widely applicable organic reaction that involves the shift of a sigma bond across the pi-system of an allyl vinyl ether to produce allylated phenols. In this project, we aim to develop a microwave assisted allylation of a phenol, followed by a subsequent Claisen rearrangement in one pot. The goals of this project are three-fold. First, we aim to accelerate these reactions using microwave assisted organic synthesis because to date, microwave technology has been sparsely used in Claisen chemistry. Second, we aim to perform these reactions in a single pot, enhancing the simplicity and elegance of the reaction. Finally, our research group has an interest in allylated phenols given the allyl group can be used to attach the ring to other molecules. Acetaminophen was chosen as a model phenol to test the chemistry. As a result, this also affords derivatives which like acetaminophen, could have analgesic properties. Initial studies reveal that the Claisen rearrangement of allylated acetaminophen requires a reaction time of under ten minutes in the microwave compared to hours when performed under reflux. Further optimization of other components of the reaction are ongoing.