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

HRID 2177044Notes

Reaction equation

HRID 2177044 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

Conditions

Temperature
0 °C

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 cooled (0° C.), 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. customquenched with sat. ammonium chloride solution
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d12214f81f6c452f8332937586ccc304
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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