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

HRID 1418484Notes

Reaction equation

HRID 1418484 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 magnesium 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 magnesium sulfate
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-5b83cc32a1294c9a8cb06293ee98a4f0
Source dataset
uspto-grants-1999_03
Patent number
US05883106

Reaction notes

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