Formic Acid → 3,5-Difluoro-4-methoxybenzaldehyde

HRID 981572Notes

Reaction equation

HRID 981572 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[O:10][CH3:11])[C:5]#N.C(O)=[O:14]>>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[O:10][CH3:11])[CH:5]=[O:14]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 105832533,5-Difluoro-4-methoxybenzonitrile

Product 1

HCID 144508603,5-Difluoro-4-methoxybenzaldehydeYield 95%

Procedure

A mixture of 3,5-difluoro-4-methoxybenzonitrile (3.50 g, 0.0207 mole) and Raney catalyst powder (3.5 g) in 90% formic acid (35 ml) was stirred and heated under reflux for 2.5 hours and the catalyst was filtered and washed with hot water and hexane. The hexane layer was separated and the aqueous solution was extracted an additional three times with hexane. The combined hexane extracts were washed with water and brine, dried and the solvent was removed to give 3,5-difluoro-4-methoxybenzaldehyde as an oil (3.38 g, 95%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2.5 hours
  3. filtrationthe catalyst was filtered
  4. washwashed with hot water and hexane
  5. customThe hexane layer was separated
  6. extractionthe aqueous solution was extracted an additional three times with hexane
  7. washThe combined hexane extracts were washed with water and brine
  8. customdried
  9. customthe solvent was removed

Sources & evidence

ORD record
ord-bf1903ab89e045b9b7eecbcb940abc96
Source dataset
uspto-grants-1991_02
Patent number
US04992459

Reaction notes

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