Ethyl Acetate → HCID 54131635, compound

HRID 2052159Notes

Reaction equation

HRID 2052159 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[N+:7]([C:10]1[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=1)[CH:13]=[C:14]([CH2:18][CH3:19])[C:15]([OH:17])=[O:16])([O-:9])=[O:8].[C:23]([O:26][CH2:27][CH3:28])(=O)C>>[N+:7]([C:10]1[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=1)[CH:13]=[C:14]([CH2:18][CH3:19])[C:15]([O:17][C:10]1[CH:11]=[CH:28][C:27]([O:26][CH3:23])=[CH:21][CH:22]=1)=[O:16])([O-:9])=[O:8]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 24819Phosphorus pentachlorideHCID 990102-[(3-Nitrophenyl)methylene]butanoic acid

Product 1

HCID 54131635HCID 54131635, compound

Procedure

Phosphorus pentachloride (22 g) was added to 22.1 g of m-nitro-α-ethylcinnamic acid suspended in 300 ml of ethyl acetate, and the mixture was stirred at room temperature for 1 hour. After the reaction, the solvent was distilled off under reduced pressure, upon which m-nitro-α-ethylcinnamoyl chloride precipitated. This compound was dissolved in 300 ml of ethyl acetate, and 12.4 g of p-methoxyphenol was added thereto. After the 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 p-methoxyphenyl m-nitro-α-ethylcinnamate. Yield: 30.7 g (93.9%); melting point: 65°-66° C.; IR (cm-1): 1710, 1503, 1351.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off under reduced pressure, upon which m-nitro-α-ethylcinnamoyl chloride
  3. customprecipitated
  4. dissolutionThis compound was dissolved in 300 ml of ethyl acetate
  5. addition12.4 g of p-methoxyphenol was added
  6. customAfter the reaction at room temperature for 1 hour
  7. washthe 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 then distilled off under reduced pressure

Sources & evidence

ORD record
ord-ff15c44c33c2419c93695fdbc8ec7b2a
Source dataset
uspto-grants-1980_01
Patent number
US04182897

Reaction notes

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