Reaction #2186216

Reaction equation

sodium hydroxide

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

hydrochloric acid

→

Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-hydroxypropane-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 in vacuum
5. 5
   workup.ADDITIONafter which 270 g of dichloromethane was added to the residue
6. 6
   WashThe organic layer was washed with 40 g of water three times
7. 7
   ConcentrationThe organic layer was concentrated
8. 8
   workup.ADDITION60 g of diethyl ether was added to the
9. 9
   Concentrationconcentrate for crystallization
10. 10
    FiltrationThe crystals were filtered
11. 11
    Otherdried
12. 12
    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 the solution was stirred under ice cooling, 54.0 g of 5% sodium hydroxide solution was added dropwise at a temperature below 10° C. It was allowed to mature 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 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, and 60 g of diethyl ether was added to the concentrate for crystallization. The crystals were filtered and dried, obtaining the target compound. White crystals, 24.3 g (yield 85%).

Source