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

HRID 491250Notes

Reaction equation

HRID 491250 reaction equation
[C:1]([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:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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>[C:1]([O:9][CH:10]([C:18]([F:20])([F:21])[F:19])[C:11]([F:16])([F:17])[S:12]([O-:15])(=[O:14])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[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.[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

6

Reactant 3

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

Product 2

HCID 23118490Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-benzoyloxypropane-1-sulfonateHCID 86612198HCID 86612198, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. customas synthesized by a standard technique
  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. additionafter which 60 g of diisopropyl ether was added to the residue for crystallization
  9. filtrationThe crystals were filtered
  10. customdried

Sources & evidence

ORD record
ord-b179976a5f1d4e138dd0fb019b92a8aa
Source dataset
uspto-grants-2009_05
Patent number
US07531290B2

Reaction notes

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