4-Fluoromandelic acid → 1-(4-Fluorophenyl)ethane-1,2-diol

HRID 2177060Notes

Reaction equation

HRID 2177060 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7](O)=[O:8])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([OH:10])[CH2:7][OH:8])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 980684-Fluoromandelic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 114125091-(4-Fluorophenyl)ethane-1,2-diolYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-fluoromandelic acid (1.0 g, 5.88 mmol) in tetrahydrofuran was added lithium aluminum hydride (0.47 g, 12.34 mmol). The reaction mixture was refluxed for 1.5 hours. The reaction mixture was quenched with sat. ammonium chloride solution, filtered, concentrated to yield 0.87 g of 1-(4-fluorophenyl)ethane-1,2-diol.

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 hours
  2. customThe reaction mixture was quenched with sat. ammonium chloride solution
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-076537da4762494b8457e4cf1c9aa66f
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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