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

HRID 1672654Notes

Reaction equation

HRID 1672654 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]([CH2:7][OH:8])[CH:11]=1

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 alcoholYield 92.6%

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. At 0° C., 4.38 ml (4.38 mmol) of a 1 M lithium aluminum hydride solution 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% yield) 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-4f07489caec649d29bb7f4114ad44d94
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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