Sodium borohydride → 2,5-Difluoro-3-methoxybenzyl alcohol

HRID 1108095Notes

Reaction equation

HRID 1108095 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([F:14])=[CH:8][C:5]=1[CH:6]=[O:7]>C(O)C>[F:3][C:4]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([F:14])=[CH:8][C:5]=1[CH2:6][OH:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 112060352,5-Difluoro-3-methoxybenzaldehyde

Product 1

HCID 114466172,5-Difluoro-3-methoxybenzyl alcoholYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (2.83 g, 74.7 mmol) was added to a stirred solution of 2,5-difluoro-3-methoxybenzaldehyde (8.57 g, 49.8 mmol) in ethanol (100 ml) at room temperature. After 30 min, the mixture was concentrated, the residue was diluted with ether (300 ml) and successively washed with water (200 ml), 10% citric acid (200 ml), water (200 ml), brine (200 ml), and dried over magnesiun sulfate. Removal of solvent gave 8.26 g (95%) of the titled compound as a white solid.

Workup

  1. concentrationthe mixture was concentrated
  2. additionthe residue was diluted with ether (300 ml)
  3. washsuccessively washed with water (200 ml), 10% citric acid (200 ml), water (200 ml), brine (200 ml)
  4. dry with materialdried over magnesiun sulfate
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-7f49d49131654df69adbc4706319548a
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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