4-Nitrophenol → (4'-Nitrophenyl)-4-nitrocinnamate

HRID 2120317Notes

Reaction equation

HRID 2120317 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10](Cl)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)([O-:17])=[O:16].N1C=CC=CC=1>CC(C)=O>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:10](=[O:11])[CH:9]=[CH:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 1049PyridineHCID 3194633-(4-nitrophenyl)prop-2-enoyl Chloride

Product 1

HCID 53711113(4'-Nitrophenyl)-4-nitrocinnamateYield 95.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
50 °C

Procedure

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 mixtures, the reaction mixtures were refluxed with stirring until the generation of hydrogen chloride gas stopped. The reacted solution was concentrated until a solid could be precipitated and was poured into hexane and then the precipitated solid was separated by filtration and dried. 210 g of 4-nitrocinnamoyl chloride was yielded. 64.5 g (0.3 mole) of 4-nitrocinnamoyl chloride and 300 g of acetone were placed in a reaction vessel. The reaction mixtures were heated at 50° C. with stirring under a nitrogen current. 41.73 g (0.3 mole) of 4-nitrophenol, 60 g of pyridine, and 300 g of acetone were added dropwise to the above reaction vessel using a dropping funnel. After the completion of the addition, the reaction mixtures were refluxed with stirring under a nitrogen current for 2 hours. After the reaction, a precipitate was separated by filtration, and the filtrated solid was washed by water and dried. 90 g of light yellow colored needle-like crystals ((4-nitrophenyl)-4-cinnamate)was yielded.

Workup

  1. customThe reaction mixtures
  2. additionAfter the completion of the addition
  3. customthe reaction mixtures
  4. temperaturewere refluxed
  5. stirringwith stirring under a nitrogen current for 2 hours
  6. customAfter the reaction
  7. customa precipitate was separated by filtration
  8. washthe filtrated solid was washed by water
  9. customdried

Sources & evidence

ORD record
ord-4e8fc877538341dc85e53ac69f21d830
Source dataset
uspto-grants-2004_02
Patent number
US06689899B2

Reaction notes

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