Water → HCID 23497057, compound

HRID 1837261Notes

Reaction equation

HRID 1837261 reaction equation
[F:1][C:2]([F:26])([C:10]([F:25])([F:24])[C:11]([F:23])([F:22])[C:12]([F:21])([F:20])[C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.O>N1C=CC=CC=1>[S:33]([C:30]1[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=1)([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([F:26])([F:1])[C:10]([F:24])([F:25])[C:11]([F:22])([F:23])[C:12]([F:20])([F:21])[C:13]([F:18])([F:19])[C:14]([F:15])([F:16])[F:17])(=[O:35])=[O:34]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 27761656-(Perfluorohexyl)hexanol

Product 1

HCID 23497057HCID 23497057, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.76 ml of 7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluoro-dodecan-1-ol is dissolved in 20 ml of absolute pyridine, mixed at 0° C. with 2.48 g of p-toluenesulfonyl chloride and stirred for 3 hours under cold conditions. Then, the reaction mixture is stirred into water, extracted with dichloromethane, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Column-chromatographic purification on silica gel with a hexane-ethyl acetate gradient yields 4.33 g of 7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluoro-dodecyl tosylate as a clear oil.

Workup

  1. extractionextracted with dichloromethane
  2. customdried on magnesium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customColumn-chromatographic purification on silica gel with a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-994864cbe4b541b5ad180ea18e60889c
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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