Water → 2-[2-(2,2,2-Trifluoroethoxy)phenoxy]ethanol

HRID 273851Notes

Reaction equation

HRID 273851 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:25])([F:24])[CH2:9][O:10][C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[O:13][CH2:14][C:15](OCC)=[O:16].S([O-])([O-])(=O)=O.[Na+].[Na+].O>O1CCCC1>[F:7][C:8]([F:24])([F:25])[CH2:9][O:10][C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[O:13][CH2:14][CH2:15][OH:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 20094388Ethyl 2-(2,2,2-trifluoroethoxy)phenoxyacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 107761632-[2-(2,2,2-Trifluoroethoxy)phenoxy]ethanolYield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (79 mg) in dry tetrahydrofuran (1 ml) was added dropwise a solution of ethyl 2-(2,2,2-trifluoroethoxy)phenoxyacetate (270 mg) in dry tetrahydrofuran (3 ml) with stirring under ice cooling, and the mixture was reacted at room temperature for 40 minutes. To the reaction mixture were added anhydrous sodium sulfate and water with stirring. The insoluble materials were filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and ethyl acetate (2/1) as eluent to give 213 mg of 2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethanol as an oil.

Workup

  1. customthe mixture was reacted at room temperature for 40 minutes
  2. stirringwith stirring
  3. filtrationThe insoluble materials were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by medium pressure liquid column chromatography on silica gel using
  6. additiona mixture of hexane and ethyl acetate (2/1) as eluent

Sources & evidence

ORD record
ord-8825241acf734dd38d38d6bf68608eba
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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