2,2,2-Trifluoroethanol → Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)

HRID 1405947Notes

Reaction equation

HRID 1405947 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].C(N(CC)CC)C.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>ClCCl>[F:1][C:2]([F:6])([F:5])[CH2:3][O:4][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)Yield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.1 ml of 2,2,2-trifluoroethanol and 4.4 ml of triethylamine were added to 100 ml of dichloromethane, and 5.0 g of p-toluenesulfonyl chloride in batches under ice-bath condition. Upon the end of the addition, the mixture was warmed to room temperature and stirred overnight. The mixture was washed with water and then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and distilled to remove the solvent to obtain 5.9 g of light yellow oily liquid, yield 98.7%.

Workup

  1. additionUpon the end of the addition
  2. washThe mixture was washed with water
  3. dry with materialwith saturated sodium chloride solution, dried over anhydrous sodium sulfate
  4. distillationdistilled
  5. customto remove the solvent

Sources & evidence

ORD record
ord-fefc1a134aa4402dbc7cf52a1246d8bb
Source dataset
uspto-grants-2014_12
Patent number
US08916574B2

Reaction notes

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