Phosphorus pentachloride → HCID 54311656, compound

HRID 2052157Notes

Reaction equation

HRID 2052157 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[N+:7]([C:10]1[CH:20]=[CH:19][C:13]([CH:14]=[CH:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1)([O-:9])=[O:8]>C(OCC)(=O)C>[N+:7]([C:10]1[CH:11]=[CH:12][C:13]([CH:14]=[CH:15][C:16]([O:18][C:10]2[CH:20]=[CH:19][C:13]([CH3:14])=[CH:12][CH:11]=2)=[O:17])=[CH:19][CH:20]=1)([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 701562-Propenoic acid, 3-(4-nitrophenyl)-

Product 1

HCID 54311656HCID 54311656, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus pentachloride (22 g) was added to 19.3 g of p-nitrocinnamic acid suspended in 300 ml of ethyl acetate, and the resulting suspension was stirred at room temperature for 1 hour. After the reaction, the solvent was removed by distillation under reduced pressure. The resulting precipitates of p-nitrocinnamoyl chloride were dissolved in 300 ml of ethyl acetate and 10.8 g of p-methylphenol was added to the resulting solution, after which 12 g of triethylamine was slowly added thereto at room temperature with constant stirring. After the mixture was subjected to reaction at room temperature for 1 hour, the reaction mixture was washed with 10% HCl, 10% NaOH and water in this order and dried on anhydrous magnesium sulfate. Then the solvent was removed by distillation under reduced pressure, whereby p-methylphenyl p-nitrocinnamate was obtained. Yield: 26.8 g (95%); melting point: 168°-170° C.; IR (cm-1): 1720, 1510, 1345. HCl).

Workup

  1. customAfter the reaction
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe resulting precipitates of p-nitrocinnamoyl chloride
  4. dissolutionwere dissolved in 300 ml of ethyl acetate
  5. addition10.8 g of p-methylphenol was added to the resulting solution
  6. additionafter which 12 g of triethylamine was slowly added
  7. customat room temperature
  8. customAfter the mixture was subjected to reaction at room temperature for 1 hour
  9. washthe reaction mixture was washed with 10% HCl, 10% NaOH and water in this order
  10. dry with materialdried on anhydrous magnesium sulfate
  11. customThen the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-dded136c233848b1b15f9e299b3009e1
Source dataset
uspto-grants-1980_01
Patent number
US04182897

Reaction notes

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