Dimethyl Sulfate → Phenyldimethylsulfonium methylsulfate

Participants

Reaction Steps

To 24.8 g of thioanisole heated to 90° C., 27.8 g of (0.22 mole) of dimethylsulfate was added dropwise with stirring over 30 minutes, while maintaining its temperature at 90°-95° C. Stirring of the mixture at the same temperature for 30 minutes resulted in quantitative formation of phenyldimethylsulfonium methylsulfate (sulfonium salt) which formed a solid mass at room temperature. The solid mass was dissolved in 110 ml of hot dichloromethane, then cooled to 0° C. with stirring to afford a suspended solution of the sulfonium salt which was employed in the following reaction.

Provenance & Evidence