Hydrochloric Acid → 1-(3,5-Bis(trifluoromethyl)phenyl)ethanol

HRID 1442511Notes

Reaction equation

HRID 1442511 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1)=[O:3].[BH4-].[Na+].Cl>CO>[F:11][C:10]([F:12])([F:13])[C:8]1[CH:9]=[C:4]([CH:2]([OH:3])[CH3:1])[CH:5]=[C:6]([C:14]([F:15])([F:16])[F:17])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1216161-(3,5-Bis(trifluoromethyl)phenyl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 64257391-(3,5-Bis(trifluoromethyl)phenyl)ethanolYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-bis(trifluoromethyl)acetophenone (2.00 g, 7.81 mmol) in methanol (20 mL) was added sodium borohydride (591 mg, 15.6 mmol) with stirring on an ice bath, and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was added with 1 M hydrochloric acid on an ice bath until pH became 7 or lower, and then concentrated under reduced pressure, the resulting residue was added with water (20 mL), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 1-[3,5-bis(trifluoromethyl)phenyl]ethanol (2.00 g, 99%) as a colorless solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. concentrationlower, and then concentrated under reduced pressure
  3. additionthe resulting residue was added with water (20 mL)
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ada179383d924a14acc049f0a17f809d
Source dataset
uspto-grants-2010_02
Patent number
US07659271B2

Reaction notes

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