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

HRID 2177056Notes

Reaction equation

HRID 2177056 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-0384710f2a0a4d3c94d8d994b4e1caec
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

Loading…