Pyridine → 3,5-Dinitrophenyl cinnamate

HRID 2120312Notes

Reaction equation

HRID 2120312 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:16]=[C:17]([OH:24])[CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)([O-:14])=[O:13].N1C=CC=CC=1>CC(C)=O>[C:1]([O:24][C:17]1[CH:16]=[C:15]([N+:12]([O-:14])=[O:13])[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=1)(=[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 114593,5-DinitrophenolHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 3182223,5-Dinitrophenyl cinnamateYield 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 3,5-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 2 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-0fec1c9e49e14b37bfa8323f97eacba2
Source dataset
uspto-grants-2004_02
Patent number
US06689899B2

Reaction notes

Loading…