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

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 mL of 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.

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
9. dry with materialdried over sodium sulfate (Na2SO4)
10. concentrationconcentrated
11. custom(rotary evaporator)

ORD record

ord-4a1fed729dc5422ead9ff8d08f38bde2

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05773450