1-(4-Nitrophenyl)-2,2,2-trifluoroethane-1,1-diol → 1-(4-Aminophenyl)-2,2,2-trifluoroethan-1-ol

HRID 28615Notes

Reaction equation

HRID 28615 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)(O)[OH:4].[H][H]>[Pd].C(O)C>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([CH:3]([OH:4])[C:2]([F:1])([F:15])[F:16])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 689875671-(4-Nitrophenyl)-2,2,2-trifluoroethane-1,1-diolHCID 178418361HCID 178418361, compound

Product 1

HCID 126403421-(4-Aminophenyl)-2,2,2-trifluoroethan-1-olYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,2,2-trifluoro-1-(4-nitro-phenyl)-ethane-1,1-diol (1.1 g, 4.6 mmol), palladium on carbon (100 mg, 10%), and ethanol (50 ml) was treated with hydrogen gas on a Parr shaker (50 psi) for 1 hour. The mixture was filtered through celite under suction and the filtrate was concentrated under reduced pressure to afford 1-(4-amino-phenyl)-2,2,2-trifluoro-ethanol (100% yield).

Workup

  1. filtrationThe mixture was filtered through celite under suction
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-696c629a557b4901889af49d7379380b
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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