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

HRID 355556Notes

Reaction equation

HRID 355556 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

In a bomb tube (pressurized vessel), 40.5 g of 3-hydroxybenzotrifluoride, 18.0 g of α-butylene oxide and 1.0 g of lithium hydroxide monohydrate are heated for 16 hours at 140° C. After the reaction vessel has cooled, the reaction mixture is dissolved in 200 ml of ethyl acetate, and the organic phase is washed with water and subsequently dried over sodium sulfate. After concentration, 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 employed in the subsequent reaction without further purification.

Workup

  1. temperatureAfter the reaction vessel has cooled
  2. washthe organic phase is washed with water
  3. dry with materialsubsequently dried over sodium sulfate
  4. concentrationAfter concentration

Sources & evidence

ORD record
ord-987c0c0333174d99907148f34b8c1d7b
Source dataset
uspto-grants-1998_11
Patent number
US05831114

Reaction notes

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