3-Fluorophenylacetic acid → 2-(3-Fluorophenyl)ethanol

HRID 440933Notes

Reaction equation

HRID 440933 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]([CH2:14][C:15](O)=[O:16])[CH:11]=[CH:12][CH:13]=1>C(OCC)C.O1CCCC1>[F:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][OH:16])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 676173-Fluorophenylacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 5731322-(3-Fluorophenyl)ethanolYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3.07 gm (81 mMol) lithium aluminum hydride in 115 mL diethyl ether at 0° C. were added dropwise a solution of 7.0 gm (45 mMol) 3-fluorophenylacetic acid in 26 mL tetrahydrofuran dropwise. The reaction was allowed to warm to ambient and then stirred 18 hours. The reaction mixture was quenched by the addition of 3.0 mL 2N NaOH dropwise with cooling. To this mixture was then added 9.0 mL water and the resulting suspension stirred for 1 hour at ambient. The suspension was filtered and the filter cake rinsed well with diethyl ether, The filtrate was concentrated under reduced pressure to give 6.26 gm (100%) of the title compound as a clear oil. The product was used without further purification.

Workup

  1. temperatureto warm to ambient and
  2. customThe reaction mixture was quenched by the addition of 3.0 mL 2N NaOH dropwise
  3. temperaturewith cooling
  4. additionTo this mixture was then added 9.0 mL water
  5. stirringthe resulting suspension stirred for 1 hour at ambient
  6. filtrationThe suspension was filtered
  7. washthe filter cake rinsed well with diethyl ether
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a367af0ed77147a7b9c1f85aec06fef7
Source dataset
uspto-grants-1996_05
Patent number
US05521197

Reaction notes

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