The Yale Undergraduate Research Journal


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.

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