Hydrochloric Acid → 3-(4-nitrophenyl)prop-2-enoyl Chloride

193.2 g (1 mole) of 4-nitrocinnamic acid and 650 g of ethyl acetate were placed in a reaction vessel. While 200 g of thionyl chloride with some drops of DMF was dropped into the reaction mixture, the reaction mixture was refluxed with stirring until the generation of hydrogen chloride gas stopped. The reacted solution was concentrated until a solid could be precipitated and then poured into hexane. The precipitated solid was separated by filtration and dried. 210 g of 4-nitrocinnamoyl chloride was yielded. 63.5 g (0.3 mole) of 4-nitrocinnamoyl chloride and 400 g of methylethylketone were placed in a reaction vessel and the reaction mixtures were stirred by heating at 50° C. under a nitrogen current. 15.42 g (0.14 mole) of resorcinol, 32 g of pyridine, and 100 g of methylethylketone were added dropwise to the above reaction vessel using a dropping funnel. After the completion of the addition, the reaction solution was refluxed with stirring under a nitrogen current for 2 hours. After the reaction, the precipitate was separated by filtration and the filtrated solid was washed by water and dried. 64 g of white colored crystals (1,3-bis (4-nitrocinnamic acid) benzene) was yielded.

1. temperaturethe reaction mixture was refluxed
2. concentrationThe reacted solution was concentrated until a solid
3. customcould be precipitated
4. additionpoured into hexane
5. customThe precipitated solid was separated by filtration
6. customdried

ORD record

ord-aadb04295fa34dabbf5832f479af1974

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06689899B2