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

HRID 1921861Notes

Reaction equation

HRID 1921861 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., then a 1 M solution of 557 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. 2 g (92% of theory) of the title compound are obtained.

Workup

  1. additionThe mixture is added to ice
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic phase is concentrated
  4. customthe crude product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3c1dba28f28f4235a2a4be32318e98d8
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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