4-(Trifluoromethyl)mandelic acid → 1-[4-(trifluoromethyl)phenyl]ethane-1,2-diol

HRID 1364478

Reaction equation

HRID 1364478 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]([OH:11])[C:8](O)=[O:9])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([CH:7]([OH:11])[CH2:8][OH:9])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 1645934-(Trifluoromethyl)mandelic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 114811481-[4-(trifluoromethyl)phenyl]ethane-1,2-diolYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-trifluoromethylmandelic acid (1.0 g, 4.54 mmol) in tetrahydrofuran was added lithium aluminum hydride (0.36 g, 9.54 mmol). The reaction mixture was refluxed for 1.5 hours. The reaction mixture was quenched with sat. ammonium chloride solution, filtered, concentrated to yield 0.8 g of 1-(4-trifluoromethylphenyl)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-ae76971e3ad2476e84f830fd308ddf1a
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Linked notes

Loading…