Acetic Acid → 3,4-Dimethoxy-beta-nitrostyrene

Participants

Reaction Steps

In a 250 mL flask was placed 42.45 g of 3,4-dimethoxybenzaldehyde (0.255 mole, 1 eq.), 64 mL of glacial acetic acid (4.0 M), 9.83 g of ammonium acetate (0.128 mole, 0.5 eq), and 15.2 mL of nitromethane (0.281 mole, 1.1 eq.). The mixture was stirred well and heated to reflux for 1.5 hour and allowed to cool to room temperature. The reaction mass solidified and was dissolved in methylene chloride (500 mL) and washed with water (2×400 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated on a rotary evaporator to provide 56.33 g of crude product. Crystallization of the product from ethanol (240 mL) and acetone (100 mL) provided 28.66 g of 2-(3,4-dimethoxypheny)-nitroethene (0.137 mole), 53.7% yield.

Provenance & Evidence