Hydrochloric Acid → 8,8,9,9,10,10,10-Heptafluoro-3,6-dioxadecyl p-toluenesulfonate

HRID 362167Notes

Reaction equation

HRID 362167 reaction equation
[F:1][C:2]([F:18])([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10].N1C=CC=CC=1.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.Cl>O>[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][C:2]([F:18])([F:1])[C:11]([F:16])([F:17])[C:12]([F:14])([F:15])[F:13])(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 149635572-[2-(2,2,3,3,4,4,4-Heptafluorobutoxy)ethoxy]ethan-1-ol

Product 1

HCID 538461308,8,9,9,10,10,10-Heptafluoro-3,6-dioxadecyl p-toluenesulfonateYield 103.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g (17.3 mM) of 8,8,9,9,10,10,10-heptafluoro-3,6-dioxadecanol and 4.8 ml of pyridine were stirred under cooling on an ice bath. To the mixture, 4.0 g (20.8 mM) of p-toluenesulfonyl chloride was added, followed by stirring for 3 hours. The reaction mixture was poured into water and acidified by hydrochloric acid, followed by extraction with ethylacetate, washing with water, drying with anhydrous sodium sulfate and distilling-off of the solvent to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=10/1) to obtain 7.92 g of 8,8,9,9,10,10,10-heptafluoro-3,6-dioxadecyl p-toluenesulfonate (Yield: 99.8%).

Workup

  1. temperatureunder cooling on an ice bath
  2. extractionfollowed by extraction with ethylacetate
  3. washwashing with water
  4. dry with materialdrying with anhydrous sodium sulfate and distilling-off of the solvent
  5. customto obtain a residue
  6. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-45231e175b5f46ba9d760931948e7d93
Source dataset
uspto-grants-1999_02
Patent number
US05868960

Reaction notes

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