Hydrochloric Acid → 2-Methoxy-1-(2-nitroethenyl)naphthalene

Participants

Reaction Steps

A mixture of 2-methoxy-1-naphthaldehyde (1862 mg, 10 mmol) and nitromethane (610 mg, 10 mmol) in methanol (200 ml) is stirred at room temperature until the solids dissolved. The solution is cooled to about 0° C. and a 30% NaOH solution (2 ml, 20 mmol) is added dropwise over 30 min. The resulting solution is added slowly at 60° C. to a 35% HCl solution (200 ml). The amorphous solid that formed is filtered and washed with water. The crude product is recrystallized from ethanol to give pure title compound in 80% yield (1835 mg).

Provenance & Evidence