Hydrochloric Acid → Triphenylsulfonium chloride

Participants

Reaction Steps

Into 400 g of dichloromethane was dissolved 40 g (0.2 mole) of diphenyl sulfoxide, and the resulting solution was agitated under ice-cool. And then, 65 g (0.6 mole) of trimethyl silyl chloride was added dropwise at the temperature not exceeding 20° C., at which temperature the mixture was aged for 30 minutes. Thereafter, a Grignard agent prepared separately from 14.6 g (0.6 mole) of a metal magnesium, 67.5 g (0.6 mol) of chlorobenzene, and 168 g of tetrahydrofurane (THF) was added dropwise into it at the temperature not exceeding 20° C. After the reaction mixture was aged for one hour, it was added by 50 g of water at the temperature not exceeding 20° C. to terminate the reaction, and then further by 150 g of water, 10 g of 12-N hydrochloric acid, and 200 g of diethyl ether. A water layer was taken out by separation and washed by 100 g of diethyl ether to obtain an aqueous triphenyl sulfonium chloride solution. This was used in the subsequent reaction without isolation procedures further.

Provenance & Evidence