Hydrochloric Acid → Triphenylsulfonium 4-hydroxy-1,1,2,2-tetrafluorobutanesulfonate

HRID 1662167Notes

Reaction equation

HRID 1662167 reaction equation
C([O:9][CH2:10][CH2:11][C:12]([F:21])([F:20])[C:13]([F:19])([F:18])[S:14]([O-:17])(=[O:16])=[O:15])(=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][CH2:10][CH2:11][C:12]([F:21])([F:20])[C:13]([F:18])([F:19])[S:14]([O-:17])(=[O:15])=[O:16].[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 86654882Triphenylsulfonium 4-benzoyloxy-1,1,2,2-tetrafluorobutanesulfonate

Product 1

HCID 86639888Triphenylsulfonium 4-hydroxy-1,1,2,2-tetrafluorobutanesulfonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 8 g of methanol was dissolved 2.1 g of triphenylsulfonium 4-benzoyloxy-1,1,2,2-tetrafluorobutanesulfonate synthesized in Synthesis Example 9. The solution was stirred under ice cooling, to which 2.5 g of a 9% sodium hydroxide aqueous solution was added dropwise at a temperature below 10° C. The solution was aged at room temperature for 70 hours, after which 22 g of 1N hydrochloric acid was added under ice cooling for quenching the reaction. The methanol was removed under vacuum. Dichloromethane was added to the organic layer, which was washed three times with water. The organic layer was concentrated and dried, obtaining the target compound. Colorless oily matter, 0.3 g.

Workup

  1. customsynthesized in Synthesis Example 9
  2. additionwas added dropwise at a temperature below 10° C
  3. customfor quenching
  4. customthe reaction
  5. customThe methanol was removed under vacuum
  6. additionDichloromethane was added to the organic layer, which
  7. washwas washed three times with water
  8. concentrationThe organic layer was concentrated
  9. customdried
  10. customobtaining the target compound

Sources & evidence

ORD record
ord-4453f01272b742c29ad58522509735cc
Source dataset
uspto-grants-2011_10
Patent number
US08030515B2

Reaction notes

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