Phosphorus pentachloride → HCID 53814857, compound

HRID 2052163Notes

Reaction equation

HRID 2052163 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[N+:7]([C:10]1[CH:11]=[C:12]([CH:19]=[CH:20][CH:21]=1)[CH:13]=[C:14]([CH3:18])[C:15]([OH:17])=[O:16])([O-:9])=[O:8]>C(OCC)(=O)C>[N+:7]([C:10]1[CH:11]=[C:12]([CH:19]=[CH:20][CH:21]=1)[CH:13]=[C:14]([CH3:18])[C:15]([O:17][C:10]1[CH:11]=[CH:12][CH:19]=[CH:20][CH:21]=1)=[O:16])([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 41802852-Propenoic acid, 2-methyl-3-(3-nitrophenyl)-

Product 1

HCID 53814857HCID 53814857, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus pentachloride (22 g) was added to 20.7 g of m-nitro-α-methylcinnamic 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 removed by distillation under reduced pressure, upon which m-nitro-α-methylcinnamoyl chloride precipitated. This was dissolved in 300 ml of ethyl acetate, and 9.4 g of phenol was added to the solution. The solution was subjected to reaction at room temperature for 1 hour. Then the reaction mixture was washed with 10% HCL, 10% NaOH and water in this order and dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, to obtain phenyl m-nitro-α-methylcinnamate in the form of a light yellow oily matter. Yield: 25.5 g (90%); IR (cm-1); 1720, 1525, 1352.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed by distillation under reduced pressure, upon which m-nitro-α-methylcinnamoyl chloride
  3. customprecipitated
  4. dissolutionThis was dissolved in 300 ml of ethyl acetate
  5. addition9.4 g of phenol was added to the solution
  6. customThe solution was subjected to reaction at room temperature for 1 hour
  7. washThen the reaction mixture was washed with 10% HCL, 10% NaOH and water in this order
  8. dry with materialdried on anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ba43f5fde90c457f8bd0d05b98af2883
Source dataset
uspto-grants-1980_01
Patent number
US04182897

Reaction notes

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