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

HRID 2121093Notes

Reaction equation

HRID 2121093 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 90 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-d3e8b7a09cbd40b6b5f4e7c32401f47b
Source dataset
uspto-grants-2004_02
Patent number
US06693223B1

Reaction notes

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