Water → 2-Fluoro-3-methoxybenzyl alcohol

HRID 1443143Notes

Reaction equation

HRID 1443143 reaction equation
[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+].O>C(O)C>[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 37744632-Fluoro-3-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 5935892-Fluoro-3-methoxybenzyl alcoholYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25.66 g (166.47 mmol) of 2-fluoro-3-methoxybenzaldehyde is dissolved in 140 ml of ethanol and mixed in portions at 0° C. with 3.15 g (83.35 mmol) of sodium borohydride. After one hour of stirring at room temperature, the reaction mixture is mixed with water and extracted three times with methyl tert-butyl ether. The combined organic extracts are shaken with water and brine, dried, the desiccant is suctioned off, and the solvent is spun off. The remaining residue is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane). 24.79 g (95.3%) of the desired compound is obtained.

Workup

  1. extractionextracted three times with methyl tert-butyl ether
  2. stirringThe combined organic extracts are shaken with water and brine
  3. customdried
  4. customThe remaining residue is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bc978c9b61604dd0bf7c2c8493b4287a
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

Loading…