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

HRID 1600197Notes

Reaction equation

HRID 1600197 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#N.C(O)=[O:16]>[Ni]>[F:1][C:2]([F:14])([F:13])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:16]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 130045632-(2,2,2-Trifluoroethoxy)benzonitrile

Product 1

HCID 47709452-(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 0.2 g (1 mmol) of 2-(2,2,2-trifluoroethoxy)benzonitrile (J. Org. Chem., 377 (1983)) and 5 mLof formic acid. To this solution was added ca. 0.2 g of Raney nickel, and the mixture was heated at reflux for 90 minutes. The mixture was filtered through diatomaceous earth, and the filter cake was rinsed with water and chloroform (CHCl3). The layers were separated, and the aqueous phase was extracted with three portions of chloroform. The combined organic fractions were washed with saturated aqueous sodium bicarbonate and water,dried over sodium sulfate (Na2SO4) and concentrated (rotary evaporator) to obtain 176 mg of the title compound as a yellow solid, m.p.33°-34° C.

Workup

  1. customUnder a nitrogen atmosphere in a round-bottom flask equipped with a reflux condenser
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 90 minutes
  4. filtrationThe mixture was filtered through diatomaceous earth
  5. washthe filter cake was rinsed with water and chloroform (CHCl3)
  6. customThe layers were separated
  7. extractionthe aqueous phase was extracted with three portions of chloroform
  8. washThe combined organic fractions were washed with saturated aqueous sodium bicarbonate and water,dried over sodium sulfate (Na2SO4)
  9. concentrationconcentrated
  10. custom(rotary evaporator)

Sources & evidence

ORD record
ord-7f769e913bc84eb7a44c1f86870b1956
Source dataset
uspto-grants-1998_04
Patent number
US05744480

Reaction notes

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