Hydrochloric Acid → Triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropanesulfonate

HRID 1914062Notes

Reaction equation

HRID 1914062 reaction equation
C([O:9][CH:10]([C:18]([F:21])([F:20])[F:19])[C:11]([F:17])([F:16])[S:12]([O-:15])(=[O:14])=[O:13])(=O)C1C=CC=CC=1.[C:22]1([S+:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[Na+].Cl>CO>[OH:9][CH:10]([C:18]([F:21])([F:19])[F:20])[C:11]([F:16])([F:17])[S:12]([O-:15])(=[O:14])=[O:13].[C:35]1([S+:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23118490Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-benzoyloxypropane-1-sulfonate

Product 1

HCID 86612198Triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropanesulfonateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 1-22. While the solution was stirred under ice cooling, 54.0 g of 5% sodium hydroxide aqueous solution was added dropwise at a temperature below 10° C. The reaction solution 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%). The compound (PAG9) had the following structure.

Workup

  1. customsynthesized in Synthesis Example 1-22
  2. customto quench
  3. customthe reaction
  4. distillationThe methanol was distilled off in vacuum
  5. additionafter which 270 g of dichloromethane was added to the residue
  6. washThe organic layer was washed with 40 g of water three times
  7. concentrationThe organic layer was concentrated
  8. addition60 g of diethyl ether was added to the
  9. concentrationconcentrate for crystallization
  10. filtrationThe crystals were filtered
  11. customdried
  12. customobtaining the target compound

Sources & evidence

ORD record
ord-c870fd2fb7d145b8b70ce5fed7637512
Source dataset
uspto-grants-2013_12
Patent number
US08609889B2

Reaction notes

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