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

HRID 1364466

Reaction equation

HRID 1364466 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-8579c96a205d49478389a5db17e9828f
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Linked notes

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