2,2,2-Trifluoroethanol → 2-(2,2,2-Trifluoroethoxy)ethan-1-ol

HRID 855603Notes

Reaction equation

HRID 855603 reaction equation
[CH2:1]([OH:6])[C:2]([F:5])([F:4])[F:3].C1(=O)O[CH2:10][CH2:9][O:8]1.C(N(CC)CC)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:3][C:2]([F:5])([F:4])[CH2:1][O:6][CH2:10][CH2:9][OH:8]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 7303Ethylene carbonateHCID 8471Triethylamine

Product 1

HCID 2558542-(2,2,2-Trifluoroethoxy)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

Trifluoroethanol (36 mL, 494 mmol), ethylene carbonate (66.0 g, 741 mmol), triethylamine (70 mL, 494 mmol) and tetrabutylammonium bromide (3.20 g, 9.90 mmol) were combined and the reaction mixture heated to reflux for 24 hours. The reaction mixture was distilled at atmospheric pressure, yielding the title product in the range 132° C. to 142° C.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 24 hours
  3. distillationThe reaction mixture was distilled at atmospheric pressure

Sources & evidence

ORD record
ord-a2e488b13a0549b6b5228bd972fae987
Source dataset
uspto-grants-2007_08
Patent number
US07262192B2

Reaction notes

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