1-(3,5-Bis(trifluoromethyl)phenyl)ethan-1-one → 1-(3,5-Bis(trifluoromethyl)phenyl)ethanol

HRID 1289950Notes

Reaction equation

HRID 1289950 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[C:5]([CH:13]([OH:15])[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 2

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

Product 1

HCID 64257391-(3,5-Bis(trifluoromethyl)phenyl)ethanolYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 17.8 g of 3',5'-bis(trifluoromethyl) acetophenone in 300 mL of absolute ethanol was added 1.32 g of NaBH4 while stirring in an ice bath. After 30 min the ice bath was removed and stirring was continued for an additional 1.5 h. The reaction was quenched using excess 2N HCl and the solvent was mostly evaporated in vacuo. The residue was partitioned between ethyl acetate and aq. HCl and the aqueous layer was extracted again with ethyl acetate. The separate organic layers were sequentially washed with brine, then combined, dried over MgSO4 and evaporated to provide 16.74 g of the title compound as a white solid after vacuum drying.

Workup

  1. customAfter 30 min the ice bath was removed
  2. stirringstirring
  3. customThe reaction was quenched
  4. customthe solvent was mostly evaporated in vacuo
  5. customThe residue was partitioned between ethyl acetate and aq. HCl
  6. extractionthe aqueous layer was extracted again with ethyl acetate
  7. washThe separate organic layers were sequentially washed with brine
  8. dry with materialdried over MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-1079012be0b24864bfb4a7a30ea47d87
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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