3,5-Difluorobenzaldehyde → 3,5-Difluorobenzyl alcohol

HRID 1595125Notes

Reaction equation

HRID 1595125 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([F:12])[CH:11]=1)[CH:7]=[O:8]>C(O)C>[F:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([F:12])[CH:11]=1)[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 5881603,5-DifluorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 5227213,5-Difluorobenzyl alcoholYield 94.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 20 g portion of sodium borohydride was suspended (partially dissolved) in 80 ml of ethanol, and 380 ml of ethanol solution containing 125 g of 3,5-difluorobenzaldehyde to the suspension which was cooled in an ice bath. After the dropwise addition, this was stirred for 1 hour, the solvent was evaporated and the resulting residue was mixed with 400 ml of water. This was extracted with 700 ml of ethyl acetate, washed with water and saturated brine in that order and then dried with anhydrous sodium sulfate. By evaporating the solvent, 120 g of 3,5-difluorobenzyl alcohol was obtained.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionAfter the dropwise addition
  3. customthe solvent was evaporated
  4. additionthe resulting residue was mixed with 400 ml of water
  5. extractionThis was extracted with 700 ml of ethyl acetate
  6. washwashed with water and saturated brine in that order
  7. dry with materialdried with anhydrous sodium sulfate
  8. customBy evaporating the solvent

Sources & evidence

ORD record
ord-24b772de2a77464cb7d8f0ccbb23507c
Source dataset
uspto-grants-2001_09
Patent number
US06287646B1

Reaction notes

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