Hydrochloric Acid → 2-(4-(Trifluoromethyl)phenyl)ethan-1-ol

HRID 1672652Notes

Reaction equation

HRID 1672652 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=[O:11])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][OH:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 112755102-(4-(Trifluoromethyl)phenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.0 g (14.7 mmol) of 4-trifluoromethylphenylacetic acid are introduced into 30 ml of abs. THF at 0° C. A 1 M solution of 557.8 mg (14.7 mmol) of lithium aluminum hydride in 14.7 ml of THF is added dropwise, and the solution is stirred at room temperature until reaction is complete. The mixture is added to ice, acidified with hydrochloric acid and extracted with ethyl acetate. The organic phase is concentrated, and the crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 6:1). 2 g (92% of theory) of the title compound are obtained.

Workup

  1. customat 0° C
  2. additionThe mixture is added to ice
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase is concentrated
  5. customthe crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 6:1)

Sources & evidence

ORD record
ord-6aec988f09bc47749e1fc4e9a6c23f4d
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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