Sodium Hydroxide → Triphenylsulfonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate

HRID 2061311Notes

Reaction equation

HRID 2061311 reaction equation
S([O-])(O)=O.[Na+].[OH-].[Na+].[F:8][C:9]([F:22])([F:21])[C:10]([OH:20])([C:16]([F:19])([F:18])[F:17])[CH2:11][S:12]([O-:15])(=[O:14])=[O:13].[Na+].[Cl-].[C:25]1([S+:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl.O>[F:19][C:16]([F:17])([F:18])[C:10]([OH:20])([C:9]([F:22])([F:8])[F:21])[CH2:11][S:12]([O-:15])(=[O:14])=[O:13].[C:38]1([S+:31]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 61343Triphenylsulfonium chlorideHCID 23665763Sodium BisulfiteHCID 59445712Sodium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate2×

Product 1

HCID 86644254Triphenylsulfonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonateYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixed solution of 18.0 g (0.10 mole) of 2,2-bistrifluoromethyloxylane, 10.4 g (0.10 mole) of sodium hydrogen sulfite, 19.3 g of water, and 0.62 g of 25% sodium hydroxide was stirred at 40° C. for 10 hours to prepare sodium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate. The obtained sodium sulfonate was used in the subsequent reaction without isolation. After sodium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate was prepared, into it were added 290 g (0.10 mole) of the triphenylsulfonium chloride aqueous solution prepared by the method of Synthesis Example 1-1 and 500 g of methylene chloride, and the resulted mixture was stirred at room temperature for 4 hours. After the stirring, the organic layer was separated, washed by water, and then concentrated under reduced pressure. Into the condensed solution was added methyl isobutyl ketone and the resulted mixture was concentrated again under reduced pressure to distil the remaining water out. Into the obtained residue was added diisopropyl ether for recrystallization. The obtained crystals were recovered and dried to obtain the intended triphenylsulfonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate (40.8 g of white crystals (yield 78%)). The structure of the intended product is shown below.

Workup

  1. customAfter the stirring, the organic layer was separated
  2. washwashed by water
  3. concentrationconcentrated under reduced pressure
  4. additionInto the condensed solution was added methyl isobutyl ketone
  5. concentrationthe resulted mixture was concentrated again under reduced pressure
  6. customto distil the remaining water out
  7. additionInto the obtained residue was added diisopropyl ether
  8. customfor recrystallization
  9. customThe obtained crystals were recovered
  10. customdried

Sources & evidence

ORD record
ord-807e7fc50195499ba41c793bee0ea31f
Source dataset
uspto-grants-2012_10
Patent number
US08283104B2

Reaction notes

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