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

HRID 1172207Notes

Reaction equation

HRID 1172207 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)Yield 79.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2,2-trifluoroethanol (5 g, 50.00 mmol) in methylene chloride (20 mL) was added 4-methylbenzene-1-sulfonyl chloride (9.4 g, 49.21 mmol). Triethylamine (15 g, 148.51 mmol) was added and the resulting solution was stirred overnight. Water (50 mL) was added and the resulting solution was extracted with methylene chloride (2×20 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford 10 g (78.7%) of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate.

Workup

  1. extractionthe resulting solution was extracted with methylene chloride (2×20 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1b91e91d7014b7fb4c73ccdad8a5792
Source dataset
uspto-grants-2010_11
Patent number
US07834004B2

Reaction notes

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