Hydrochloric Acid → Triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonate

Participants

Reaction Steps

In 760 g of methanol was dissolved 243.5 g (0.48 mole) of triphenylsulfonium 2-pivaloyloxy-1,1-difluoroethanesulfonate. To this solution under ice cooling, an aqueous solution of sodium hydroxide (40 g sodium hydroxide in 120 g water) was added dropwise at a temperature below 5° C. The reaction solution was aged at room temperature for 8 hours, and dilute hydrochloric acid (99.8 g 12N hydrochloric acid in 200 g water) was added thereto at a temperature below 10° C. to quench the reaction. The methanol was distilled off in vacuum. To the residue was added 1,000 g of dichloromethane. The organic layer was washed with 30 g of saturated saline three times and concentrated. Diisopropyl ether, 1 L, was added to the concentrate for crystallization. The crystals were filtered and dried, obtaining the target compound. 187 g (purity 78%, net yield 78%).

Provenance & Evidence