Sodium borohydride → 2-(2,2,2-Trifluoroethoxy)-5-chlorobenzyl alcohol

HRID 1935441Notes

Reaction equation

HRID 1935441 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:17])([F:16])[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:8]=1[CH:9]=[O:10]>C(O)C>[F:17][C:4]([F:3])([F:16])[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:8]=1[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 47709505-Chloro-2-(2,2,2-trifluoroethoxy)benzaldehyde

Product 1

HCID 431419322-(2,2,2-Trifluoroethoxy)-5-chlorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (200 mg, 5.3 mmol) was added to a solution of 2-(2,2,2-trifluoroethoxy)-5-chlorobenzaldehyde (2 g, 8.4 mmol) in ethanol at room temperature. After stirring for 1 hr, the solvent was removed under reduced pressure. Aqueous ammonium chloride was added to the residue to destroy excess hydride following which the mixture was extracted with ethyl acetate. The organic extracts were washed with brine and then dried over sodium sulfate. Concentration yielded the title compound as an oil: 1H NMR (CDCl3) δ7.41 (d, J=2.4 Hz, 1H), 7.25 (m, 1H), 6.77 (d, J=8.8 Hz, 1H), 4.73 (d, J=4.6 Hz, 2H), 4.40 (m, 2H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionAqueous ammonium chloride was added to the residue
  3. customto destroy excess hydride following which the mixture
  4. extractionwas extracted with ethyl acetate
  5. washThe organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationConcentration

Sources & evidence

ORD record
ord-cb1ffd1c084648b9967b2095ce057670
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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