Analysis of the Electronic Effects and Reactivity of Benzhydrols in the Formation of Benzhydryl Ethers

Authors

Katherine Quesada, Yale University
Daniel Chabeda, Yale University
Jaeger Johnson, Yale University
Alex Shore, Yale University

Abstract

Benzhydryl ethers were synthesized through the use of microwave irradiation in a proto-ionic liquid solvent. The resulting products were separated from the reaction mixture by vacuum filtration with a silica gel plug. The products were analyzed using GCMS and 1 H NMR techniques to identify and quantify products. Analysis of the resultant data indicated the syntheses of the desired benzhydryl products were successful for 4,4-dimethoxybenzhydrol (conversion: 83% (1-propyl ether), 11% (2-propyl ether), 11% (menthyl ether)) and 4,4-dimethylbenzhydrol (conversion to desired product: 100% (1-propyl ether), 100% (2-propyl ether), 26% (menthyl ether)). However, the syntheses were unsuccessful for reactant 4,4-difluorobenzhydrol and benzhydrol. It was concluded that the electron-donating groups of 4,4-dimethoxybenzhydrol and 4,4-dimethylbenzhydrol aided in the formulation of a stable intermediate and subsequent desired product. The data support the hypothesized mechanism of protonation of the hydroxyl group of the benzhydrol with subsequent creation of a carbocation intermediate.

Recommended Citation

Quesada, Katherine; Chabeda, Daniel; Johnson, Jaeger; and Shore, Alex (2021) "Analysis of the Electronic Effects and Reactivity of Benzhydrols in the Formation of Benzhydryl Ethers," The Yale Undergraduate Research Journal: Vol. 2: Iss. 1, Article 34.
Available at: https://elischolar.library.yale.edu/yurj/vol2/iss1/34