5-Nitro-2-furaldehyde diacetate

Chemical Properties

Uses

Synthesis

98-01-1

108-24-7

92-55-7

GENERAL STEPS: A premixed solution of concentrated nitric acid (8.6 mL, 12.2 g, 193.62 mmol) and concentrated sulfuric acid (0.06 mL, 1.1 g, 11.2 mmol) was slowly added dropwise under stirring conditions to acetic anhydride (90 mL) at 0 °C. Subsequently, freshly distilled 2-furancarboxaldehyde (10.4 mL, 12.06 g, 125.5 mmol) was added dropwise to the above reaction mixture over 45 minutes and stirring was continued at 0 °C for 1 hour. Upon completion of the reaction, water (100 mL) was added to the mixture and stirred at room temperature for 30 min to promote the formation of a white precipitate. Next, the pH of the reaction mixture was adjusted to about 2.5 with 10% NaOH solution, followed by heating the mixture at 50 °C for 1 hour. After the reaction solution was cooled to room temperature, the white precipitate formed was collected by filtration, washed with water, and finally recrystallized by anhydrous ethanol and dried to afford 5-nitrofurfural diacetate (Product 2) in a yield of 24.84 g in 82% yield.

References