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

HRID 466801Notes

Reaction equation

HRID 466801 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].C(N(CC)CC)C.C1(=O)O[CH2:17][CH2:16][O:15]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]([F:6])([F:5])[CH2:3][O:4][CH2:17][CH2:16][OH:15]

Participants

5

Reactant 3

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

Product 1

HCID 2558542-(2,2,2-Trifluoroethoxy)ethan-1-olYield 61%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

2,2,2-Trifluoroethanol (10.0 g, 0.10 mol), triethylamine (10.1g, 0.10 mol), ethylene carbonate (13.2 g, 0.15 mol) and tetrabutyl ammonium iodide (0.74 g) were heated in a flask fitted with a reflux condenser under nitrogen in an oil bath at 100° C. for 1 day. The triethylamine and unreacted alcohol were removed by distillation. The product 2-(2,2,2-trifluoroethoxy)ethanol, b.p. 138° C., was obtained in 61% yield (8.6 g) of 97% pure material.

Workup

  1. customfitted with a reflux condenser under nitrogen in an oil bath at 100° C. for 1 day
  2. customThe triethylamine and unreacted alcohol were removed by distillation

Sources & evidence

ORD record
ord-8f61e9721d4441aba2d17d72b8a13361
Source dataset
uspto-grants-1992_10
Patent number
US05157159

Reaction notes

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