Hydrochloric Acid → 5-Fluoro-2-[2-(4-trifluoromethylphenyl)ethoxy]benzyl alcohol

HRID 1921863Notes

Reaction equation

HRID 1921863 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=2)=[C:6]([CH:11]=1)[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 57864408Methyl 5-fluoro-2-[2-(4-trifluoromethylphenyl)ethoxy]benzoate

Product 1

HCID 578644135-Fluoro-2-[2-(4-trifluoromethylphenyl)ethoxy]benzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.0 g (5.84 mmol) of methyl 5-fluoro-2-[2-(4-trifluoromethylphenyl)ethoxy]benzoate are introduced into 25 ml of THF, then at 0° C., 4.38 ml (4.38 mmol) of a 1 M solution of lithium aluminum hydride in THF are added dropwise, and the mixture is stirred at RT until reaction is complete. The mixture is added to ice-water, acidified with hydrochloric acid and extracted with ethyl acetate. All the volatile components are removed in vacuo, and the crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1). 1.7 g (82% of theory) of the title compound are obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customAll the volatile components are removed in vacuo
  3. customthe crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-952bfe3dfd8b4e26ab4cee786fbc4b4b
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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