Formic Acid → 2-Formylamino-4-methylphenol

To 2-amino-p-cresol (8.01 g, 65 mmol) was added formic acid (5.98 g, 130 mmol) and the mixture was refluxed for 1 hour. The reaction mixture was allowed to stand for cooling. After the addition of ethyl acetate, the mixture was poured into ice-cold water. The aqueous layer was neutralized with a saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel and recrystallized from ethyl acetate-hexane to give the title compound (1). Yield 8.59 g (88%).

1. temperaturethe mixture was refluxed for 1 hour
2. temperaturefor cooling
3. additionthe mixture was poured into ice-cold water
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customevaporated
8. customThe residue was purified by column chromatography on silica gel
9. customrecrystallized from ethyl acetate-hexane

ORD record

ord-b0a24a869e134496b86831a93fbe2ea1

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05308840