Hydrochloric Acid → Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-benzoyloxypropane-1-sulfonate

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Reaction Steps

First, triphenylsulfonium 2-benzoyloxy-1,1,3,3,3-pentafluoropropane-1-sulfonate was synthesized as in Synthesis Examples 9 and 10 aside from using 1,1,3,3,3-pentafluoro-2-propan-2-yl benzoate as synthesized by a standard technique. 34.4 g of triphenylsulfonium 2-benzoyloxy-1,1,3,3,3-pentafluoropropane-1-sulfonate was dissolved in 72 g of methanol, which was stirred under ice cooling. At a temperature below 10° C., 54.0 g of a 5% sodium hydroxide aqueous solution was added dropwise thereto. The reaction solution was aged for 4 hours at the temperature. At a temperature below 10° C., 6.8 g of 12N hydrochloric acid was added to quench the reaction. The methanol was distilled off in vacuum, after which 270 g of dichloromethane was added to the residue. The organic layer was washed with 40 g of water three times. The organic layer was concentrated, after which 60 g of diisopropyl ether was added to the residue for crystallization. The crystals were filtered and dried, obtaining triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropanesulfonate.

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