Nitromethane → Beta-Nitrostyrene

Participants

Reaction Steps

Under N2, 3-Methoxy-4,5-methylenedioxybenzaldehyde (928 g, 97%, w., 5 mol), Acetic acid (2.5 L), followed by ammonium acetate (664 g, 8.5 mol) and HOAc (1 L) were added to a 22-L 4-necked flask equipped with a an overhead stirrer, a thermometer and a refluxing condenser. The mixture was stirred at room temperature for 10 minutes. Nitromethane (1350 mL, 25 mol) and acetic acid (1 L) were subsequently added. The mixture was heated and stirred at 95° C. for 6 hours. The reaction was monitored with HPLC [HPLC conditions: Zorbax Rx-C8 (25 cm×4.6 mm); column temperature 35° C.; gradient elution from 5:95 to 90:10-acetonitrile:water (0.1% phosphoric acid) in 15 minutes; flow-1.5 mL/min.; UV detection at 230 nm. Retention time: 3-Methoxy-4,5-methylenedioxybenzaldehyde-9.7 min.; 4-Methoxy-6(2-nitrovinyl)-1,3-Benzodioxole-11.8 min.]. After the reaction was completed, the mixture was cooled down to room temperature and filtered. The yellow solid was washed with acetic acid (2×500 mL) and water (2×1000 mL) and the product was dried under vacuum for 3 days to give 997 g of product. (yield 89%) 1H NMR(CDCl3/300 MHz) 7.90(d, J=15.0 Hz, 1H), 7.48(d, J=15.0 Hz, 1H), 6.74(m, 2H), 6.08(s, 2H), 3.95(s, 3H) ppm.

Provenance & Evidence