Methanol → 113242-93-6

HRID 1530751Notes

Reaction equation

HRID 1530751 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[F:11][C:12]([F:26])([F:25])[CH:13]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:14](OCC)=[O:15].CO.[OH-].[K+]>CCCCCC.O1CCCC1>[C:19]1([CH:13]([C:12]([F:11])([F:25])[F:26])[CH2:14][OH:15])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 10399031HCID 10399031, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14205782113242-93-6Yield 87.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A 20% solution of diisobutylaluminium hydride in n-hexane (53.4 ml) was added, dropwise, to ethyl α-trifluoromethylphenylacetate (2.9 g; 12.5 mmol) (T. S. Everett, S. T. Purrington, C. L. Baumgardner, J. Org. Chem. 49, 3702 (1984)) in absolute tetrahydrofuran (50 ml) at about 60° C. The mixture was then allowed to rise to room temperature and stirred for an hour at this temperature. Then at a temperature of 5°-10° C., methanol (10.5 ml) followed by 10% aqueous potassium hydroxide (5.3 ml) was added, dropwise. After 1.5 hours, the mixture was filtered and the filtrate dried over sodium sulphate which was washed with ethyl acetate and the organic phase concentrated. There was obtained 2-phenyl-2-trifluoromethylethanol (2.07 g=87.1 of theory).

Workup

  1. customat about 60° C
  2. customto rise to room temperature
  3. additionwas added
  4. filtrationthe mixture was filtered
  5. dry with materialthe filtrate dried over sodium sulphate which
  6. washwas washed with ethyl acetate
  7. concentrationthe organic phase concentrated

Sources & evidence

ORD record
ord-0c16321876cb4e7e8eedff806a602e48
Source dataset
uspto-grants-2001_03
Patent number
USRE037087E1

Reaction notes

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