Sodium borohydride → 2-(4-(Trifluoromethyl)phenyl)ethan-1-ol

HRID 1992383Notes

Reaction equation

HRID 1992383 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:15])([F:14])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]=[O:13])=[CH:7][CH:6]=1>C(O)C>[F:3][C:4]([F:14])([F:15])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][OH:13])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14298210[4-(Trifluoromethyl)phenyl]acetaldehyde

Product 1

HCID 112755102-(4-(Trifluoromethyl)phenyl)ethan-1-olYield 105.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (2 g, 0.055 mol) was added at 0° C. to a solution of 4-trifluoromethyl-phenyl)-acetaldehyde (9.4 g, 0.05 mol, from step (ii) above) in 154 ml ethanol and stirred at RT overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between 50 ml 1 N HCl and 50 ml diethyl ether. Organic layer was washed with water, dried over sodium sulfate and the solvent evaporated under reduced pressure to give 10 g of the sub-title compound as a liquid. This was directly taken for next step without further purification.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between 50 ml 1 N HCl and 50 ml diethyl ether
  3. washOrganic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-cd6ee83844f3482e80fdf21ec8280d77
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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