3-(Trifluoromethyl)phenol → 2-Butanol, 1-[3-(trifluoromethyl)phenoxy]-

HRID 1608916Notes

Reaction equation

HRID 1608916 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.[CH3:12][CH2:13][CH:14]1[O:16][CH2:15]1.O.[OH-].[Li+]>C(OCC)(=O)C>[F:11][C:8]([F:9])([F:10])[C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][CH2:15][CH:14]([OH:16])[CH2:13][CH3:12]

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 78341,2-EpoxybutaneHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 113793022-Butanol, 1-[3-(trifluoromethyl)phenoxy]-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

40.5 g of 3-hydroxybenzotrifluoride, 18.0 g of α-butylene oxide and 1.0 g of lithium hydroxide monohydrate are heated in a bomb tube (pressure reactor) for 16 hours to 140° C. After cooling the reactor, the reaction mixture is dissolved in 200 ml of ethyl acetate and the organic phase is washed with water and then dried over sodium sulfate and concentrated. The desired product, 1-(3-trifluoromethylphenoxy)-2-butanol, is obtained in a yield of 54.0 g and in high purity. The product can be used in the subsequent reaction without further purification.

Workup

  1. temperatureAfter cooling the reactor
  2. washthe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1ba4fc9f9cad4977accb87f78a19ce60
Source dataset
uspto-grants-1995_03
Patent number
US05399545

Reaction notes

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