3-Nitrobenzaldehyde → Ethyl 2-Methyl-3-(3-Nitrophenyl)propenoate

HRID 66802

Reaction equation

HRID 66802 reaction equation
C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:9])C=CC=CC=1.[N+:27]([C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=O)([O-:29])=[O:28]>C1C=CC=CC=1>[CH3:9][C:8](=[CH:33][C:32]1[CH:35]=[CH:36][CH:37]=[C:30]([N+:27]([O-:29])=[O:28])[CH:31]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 79792Ethyl 2-(triphenylphosphoranylidene)propionate

Product 1

HCID 54141471Ethyl 2-Methyl-3-(3-Nitrophenyl)propenoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred slurry of 79.8 g. of triphenyl(1[ethoxycarbonyl]ethylidene)phosphorane in 300 ml. of benzene was added 30.2 g. of 3-nitrobenzaldehyde and the resulting mixture was heated under reflux overnight. The reaction mixture was cooled and the solvent was removed by evaporation in vacuo. The residue was extracted with 300 ml. of isopropyl ether. The isopropyl ether solution was filtered, and the filtrate was evaporated in vacuo. The residue was distilled under reduced pressure, giving 37.6 g. of the title product, b.p. 147°-162° C./0.25 mm Hg. The NMR spectrum (in CDCl3) showed absorptions at 1.4 (t), 2.1 (d), 4.3 (q), 7.4 (m) and 8.1 (m) ppm.

Workup

  1. temperatureunder reflux overnight
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed by evaporation in vacuo
  4. extractionThe residue was extracted with 300 ml
  5. filtrationThe isopropyl ether solution was filtered
  6. customthe filtrate was evaporated in vacuo
  7. distillationThe residue was distilled under reduced pressure
  8. customgiving 37.6 g

Sources & evidence

ORD record
ord-eadc72b7dc9343619d37a611cd20b587
Source dataset
uspto-grants-1982_08
Patent number
US04343813

Linked notes

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