2,2,2-Trifluoroethanol → Ethyl 2,2,2-trifluoroethyl carbonate

HRID 2258148Notes

Reaction equation

HRID 2258148 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[C:7](Cl)(=[O:11])[O:8][CH2:9][CH3:10].[OH-].[K+]>C(OCC)C>[C:7](=[O:11])([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[O:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 10928Ethyl chloroformateHCID 14797Potassium Hydroxide

Product 1

HCID 21263423Ethyl 2,2,2-trifluoroethyl carbonateYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a flask (5-liter volume), 2,2,2-trifluoroethanol (800 g, 8.0 mol), ethyl chlorocarbonate (867 g, 8.0 mol) and diethyl ether (1000 ml) were charged. While the flask was cooled so that the reaction was carried out at -5° C. to 0° C., a 29.5% by weight aqueous solution of potassium hydroxide (1500 g) was added dropwise to the flask for 6 hours and the mixture was stirred for 12 hours at room temperature. The ether layer was separated, washed with water, dried and distilled to give ethyl 2,2,2-trifluoroethyl carbonate as a colorless liquid (960 g, yield 70%). The chemical structure of the produced compound was determined based on the IR and NMR absorbance spectra shown in FIG. 5 and FIG. 6 respectively and the mass spectrometry spectrum (M/e: 172).

Workup

  1. temperatureWhile the flask was cooled so that the reaction
  2. customwas carried out at -5° C. to 0° C.
  3. customThe ether layer was separated
  4. washwashed with water
  5. customdried
  6. distillationdistilled

Sources & evidence

ORD record
ord-0fef779d19784ab8a96010842ecf6558
Source dataset
uspto-grants-1997_08
Patent number
US05659062

Reaction notes

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