Phenol → Phenyl p-nitrocinnamate

HRID 2052158Notes

Reaction equation

HRID 2052158 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:21]1(O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>C(OCC)(=O)C>[N+:7]([C:10]1[CH:11]=[CH:12][C:13]([CH:14]=[CH:15][C:16]([O:18][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:17])=[CH:19][CH:20]=1)([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 996PhenolHCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 701562-Propenoic acid, 3-(4-nitrophenyl)-

Product 1

HCID 47098254Phenyl p-nitrocinnamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

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 mixture was stirred at room temperature for 1 hour. After the reaction, the solvent was distilled off under reduced pressure, upon which p-nitrocinnamoyl chloride precipitated. The precipitates thus obtained were dissolved in 300 ml of ethyl acetate, and 9.4 g of phenol was added to the resulting solution, after which 12 g of triethylamine was slowly added thereto at room temperature with stirring. After 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. The solvent was then distilled off under reduced pressure, to obtain phenyl p-nitrocinnamate. Yield: 25.5 g (95%); melting point: 151°-152° C.; IR (cm-1): 1720, 1529, 1345.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off under reduced pressure, upon which p-nitrocinnamoyl chloride
  3. customprecipitated
  4. customThe precipitates thus
  5. customobtained
  6. stirringat room temperature with stirring
  7. customAfter reaction at room temperature for 1 hour
  8. washthe reaction mixture was washed with 10% HCl, 10% NaOH and water in this order
  9. dry with materialdried on anhydrous magnesium sulfate
  10. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-25433df8ae75466096480618c0805963
Source dataset
uspto-grants-1980_01
Patent number
US04182897

Reaction notes

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