The synthesis of fragrant esters is a popular experiment for the organic chemistry laboratory course as it provides the students with a more tangible experience that heightens the relevance of the lab. A common lab that fulfills this criterion is the synthesis of methyl salicylate (wintergreen) from salicylic acid or aspirin tablets; however, the experiment is low yielding unless run for an extended period of time (24 h). We investigated the Fischer esterification of <i>trans</i>-cinnamic acid to <i>trans</i>-methyl cinnamate as a potential alternative. The starting material has the scent of honey and the product possesses a potent strawberry odor. Both compounds are natural products that are used as fragrances and flavorings. Optimization of the reaction conditions, a comparison to other published esterification labs, and the student feedback on the experiment will be presented.

Transforming honey into strawberries: The Fischer esterification of cinnamic acid to methyl cinnamate as an engaging experiment for the second-year organic chemistry laboratory.

2019 Spring National Meeting

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