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