Formic Acid → 5-Chloro-2-(2,2,2-trifluoroethoxy)benzaldehyde

HRID 965013Notes

Reaction equation

HRID 965013 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[C:6]([CH:9]=1)[C:7]#N.C(O)=[O:17]>[Ni]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[C:6]([CH:9]=1)[CH:7]=[O:17]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 190751615-Chloro-2-(2,2,2-trifluoroethoxy)benzonitrile

Product 1

HCID 47709505-Chloro-2-(2,2,2-trifluoroethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Under a nitrogen atmosphere, in a round-bottom flask equipped with a reflux condenser were placed 400 mg (1.7 mmol) of the above nitrile and 10 ml of formic acid. To the system were added ca. 500 mg of Raney nickel and the mixture was heated at ref lux for 6 hours and stirred at room temperature overnight. The mixture was filtered through a pad of a diatomaceous earth, and the pad was rinsed with water and CHCl3. The layers were separated and the aqueous phase was extracted with three portions of CHCl3. The combined organic fractions were dried and concentrated to obtain 270 mg of the title compound.

Workup

  1. customUnder a nitrogen atmosphere, in a round-bottom flask equipped with a reflux condenser
  2. temperaturethe mixture was heated at ref lux for 6 hours
  3. filtrationThe mixture was filtered through a pad of a diatomaceous earth
  4. washthe pad was rinsed with water and CHCl3
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with three portions of CHCl3
  7. customThe combined organic fractions were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-457290b3d0e14e1daaa0fa081e0a8e67
Source dataset
uspto-grants-1998_06
Patent number
US05773450

Reaction notes

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