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

Temperature

50 °C

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.

1. customfitted with a reflux condenser, a mechanical stirrer
2. customa long thermometer, and provided with an argon atmosphere
3. customformed in the reaction
4. waitAfter that period
5. temperaturethe mixture was refluxed for about 2 hours
6. concentrationthe solution was concentrated to about 2500 ml
7. distillationby distilling off a quantity of the acetic acid
8. temperatureCooling of the mixture
9. customgave an orange solid, which
10. filtrationwas then filtered
11. customdried
12. customThe product of Formula 21 was recrystallized
13. customto give bright yellow needles, which
14. filtrationwere filtered
15. customdried in a vacuum oven at about 70° C

ORD record

ord-cc99a145cce041279ca1333262cc95f0

Source dataset

uspto-grants-1994_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05326661