Hydrochloric Acid → 6-(Perfluoroethyl)hexyl p-toluenesulfonate

HRID 2297326Notes

Reaction equation

HRID 2297326 reaction equation
[F:1][C:2]([F:14])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[C:3]([F:6])([F:5])[F:4].N1C=CC=CC=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.Cl>O>[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:2]([F:14])([F:1])[C:3]([F:5])([F:4])[F:6])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 27759497,7,8,8,8-Pentafluorooctan-1-ol

Product 1

HCID 130082316-(Perfluoroethyl)hexyl p-toluenesulfonateYield 73.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a reaction vessel, 5.00 g (22.7 mmol) of 6-(perfluoroethyl)hexanol (1) and 6.3 ml of pyridine were placed, and 5.21 g (27.3 mmol) of p-toluene-sulfonyl chloride was added little by little thereto under stirring and cooling with ice. After the addition, the system was stirred for 6 hours. The reaction product was poured into iced water, acidified by addition of 6 ml of hydrochloric acid and then extracted with chloroform. The organic layer was washed with salt water and dried with sodium sulfate, followed by solidification by removal of the solvent under a reduced pressure. The residue was purified by silica gel column chromatography with eluents of hexane/toluene=2/1, toluene, and toluene/ethyl acetate=5/1, successively, having increasing polarity, thereby obtaining 6.23 g (yield=73.3%) of 6-(perfluoroethyl)hexyl p-toluenesulfonate (2).

Workup

  1. temperaturecooling with ice
  2. additionAfter the addition
  3. stirringthe system was stirred for 6 hours
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with salt water
  6. dry with materialdried with sodium sulfate
  7. customfollowed by solidification by removal of the solvent under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography with eluents of hexane/toluene=2/1, toluene, and toluene/ethyl acetate=5/1
  9. temperaturesuccessively, having increasing polarity

Sources & evidence

ORD record
ord-87992df5691948d1b3f730cc2a194da8
Source dataset
uspto-grants-2002_12
Patent number
US06491847B1

Reaction notes

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