Reaction #312588

Reaction equation

sodium hydroxide

triphenylsulfonium 2-benzoyloxy-1,1,3,3,3-pentafluoropropane-1-sulfonate

hydrochloric acid

→

triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropane-1-sulfonate

Yield 85.0%

Solvents

methanol

Conditions

Workup

1. 1
   Othersynthesized in Synthesis Example 10
2. 2
   Otherto quench
3. 3
   Otherthe reaction
4. 4
   workup.DISTILLATIONThe methanol was distilled off under vacuum, and 270 g of dichloromethane
5. 5
   workup.ADDITIONwas added
6. 6
   WashThe organic layer was washed with 40 g of water three times
7. 7
   ConcentrationThe organic layer was then concentrated
8. 8
   workup.ADDITION60 g of diethyl ether was added to the residue for crystallization
9. 9
   FiltrationThe crystals were filtered
10. 10
    Otherdried
11. 11
    Otherobtaining the target compound

Procedure

In 72 g of methanol was dissolved 34.4 g of triphenylsulfonium 2-benzoyloxy-1,1,3,3,3-pentafluoropropane-1-sulfonate synthesized in Synthesis Example 10. While stirring under ice cooling, 54.0 g of a 5% sodium hydroxide aqueous solution was added dropwise to the solution at a temperature below 10° C. The reaction solution was aged at the temperature for 4 hours. At a temperature below 10° C., 6.8 g of 12N hydrochloric acid was added to quench the reaction. The methanol was distilled off under vacuum, and 270 g of dichloromethane was added. The organic layer was washed with 40 g of water three times. The organic layer was then concentrated and 60 g of diethyl ether was added to the residue for crystallization. The crystals were filtered and dried, obtaining the target compound. White crystals, 24.3 g (yield 85%).

Source