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

HRID 2110153Notes

Reaction equation

HRID 2110153 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-660924aee5be4f1fbe4e4ef548d079cd
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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