Water → 3-(1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl)propan-1-ol

HRID 217546Notes

Reaction equation

HRID 217546 reaction equation
[F:1][C:2]([F:18])([S:13][CH2:14][CH2:15][CH2:16][OH:17])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].ClC1C=CC=C(C(OO)=O)C=1.[OH2:30].[OH2:31].O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].O>C(Cl)Cl>[F:18][C:2]([F:1])([S:13]([CH2:14][CH2:15][CH2:16][OH:17])(=[O:31])=[O:30])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6]

Participants

6

Reactant 4

HCID 962WaterHCID 61475Sodium Thiosulfate PentahydrateHCID 70297m-Chloroperbenzoic acidHCID 860944813-[(Nonafluorobutyl)sulfanyl]propan-1-ol

Product 1

HCID 714036003-(1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl)propan-1-olYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(Perfluorobutylthio)propanol (8.60 g, 27.6 mmol) prepared in Synthetic Example 1 was dissolved in methylene chloride (80 ml), and m-chloroperbenzoic acid (m-CPBA) (52 g, 232 mmol) was added at room temperature in two portions with stirring, the reaction vessel being equipped with a calcium chloride tube. The mixture was stirred at room temperature for 7 days. The reaction mixture was injected into a mixture of sodium thiosulfate pentahydrate (130 g) and water (200 ml), and stirred for 1 hour. Methylene chloride (100 mL) was added and an organic layer was removed and an aqueous layer was extracted with methylene chloride (50 ml). Organic layers were joined, washed with a 5% aqueous sodium hydrogen carbonate and with a saturated saline solution, and then dried over sodium sulfate. A filtrate after filtration was concentrated under reduced pressure. A residue was subjected to a silica gel column chromatography (eluting solvent:hexane-ethyl acetate (2/1)), and fractions having Rf value of 0.32 [Rf value (Thin Layer Chromatography (TLC))=(Migration distance of sample)/(Migration distance of eluting solvent)] were gathered, concentrated under reduced pressure and dried under vacuum to give crystalline 3-(perfluorobutylsulfonyl)propanol (8.79 g). Yield: 91.8%.

Workup

  1. customthe reaction vessel being equipped with a calcium chloride tube
  2. stirringThe mixture was stirred at room temperature for 7 days
  3. stirringstirred for 1 hour
  4. customan organic layer was removed
  5. extractionan aqueous layer was extracted with methylene chloride (50 ml)
  6. washwashed with a 5% aqueous sodium hydrogen carbonate and with a saturated saline solution
  7. dry with materialdried over sodium sulfate
  8. filtrationA filtrate after filtration
  9. concentrationwas concentrated under reduced pressure
  10. washA residue was subjected to a silica gel column chromatography (eluting solvent:hexane-ethyl acetate (2/1)), and fractions
  11. concentrationconcentrated under reduced pressure
  12. customdried under vacuum

Sources & evidence

ORD record
ord-83270824057a41aa8d0bb93956a1a02c
Source dataset
uspto-grants-2012_06
Patent number
US08197590B2

Reaction notes

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