Acetic Acid → Phenol, 4-[2-(4-nitrophenyl)ethenyl]-

Participants

Reaction Conditions

Reaction Steps

The Schiffs base of Formula 19 (807 g, 4.098 m) , 4-nitrophenylacetic acid (Formula 20, 742 g, 4.098 m), and glacial acetic acid (3.5 liters) were charged into a 12 liter, 4 necked flask, fitted with a reflux condenser, a mechanical stirrer, and a long thermometer, and provided with an argon atmosphere. The mixture was heated to about 50° C., and stirred for about 7 days at that temperature, during when an orange solid formed in the reaction. After that period, the mixture was refluxed for about 2 hours, and the solution was concentrated to about 2500 ml by distilling off a quantity of the acetic acid. Cooling of the mixture gave an orange solid, which was then filtered, and dried. The product of Formula 21 was recrystallized from boiling acetonitrile to give bright yellow needles, which were filtered and dried in a vacuum oven at about 70° C. Yield: 693 g (70%), m.p. 208°-210° C.

Provenance & Evidence