Pyridine → 2-Propenoic acid, 3-phenyl-, 2,4-dinitrophenyl ester

HRID 380716Notes

Reaction equation

HRID 380716 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:12]([C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[OH:24])([O-:14])=[O:13].N1C=CC=CC=1>CC(C)=O>[C:1]([O:24][C:16]1[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=1[N+:12]([O-:14])=[O:13])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 14932,4-DinitrophenolHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 740530652-Propenoic acid, 3-phenyl-, 2,4-dinitrophenyl esterYield 71.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Conditions

Temperature
60 °C

Procedure

66.64 g (0.4 mole) of cinnamoyl chloride and 300 g of methyl ketone (hereinafter referred to as MEK) were placed in a reaction vessel to be stirred by heating at 60° C. under a nitrogen current. 73.64 g (0.4 mole) of 2,4-dinitrophenol, 50 g of pyridine, and 500 g of MEK were added dropwise to the above reaction vessel using a dropping funnel. After that, reflux stirring was conducted for approximately 20 hours under a nitrogen current. After the completion of the reaction, the precipitate was separated by filtration. The filtrate was concentrated until crystals separated out and poured into methanol. 90 g of light yellow colored needle-like crystals (2,4-dinitrophenyl cinnamate) were yielded.

Workup

  1. customwere placed in a reaction vessel
  2. temperatureAfter that, reflux
  3. stirringstirring
  4. customAfter the completion of the reaction
  5. customthe precipitate was separated by filtration
  6. concentrationThe filtrate was concentrated until crystals
  7. customseparated out and
  8. additionpoured into methanol

Sources & evidence

ORD record
ord-e44e1239dfd44606a773c7339484058a
Source dataset
uspto-grants-2001_10
Patent number
US06303742B1

Reaction notes

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