Ethyl Acetate → HCID 20329820, compound

HRID 2058045Notes

Reaction equation

HRID 2058045 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][CH:9]2[C:14]([OH:16])=[O:15])([O-:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)Cl.[C:23]([O:26][CH2:27][CH3:28])(=[O:25])[CH3:24]>>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][CH:9]2[C:14]([O:16][C:4]1[CH:13]=[CH:12][C:24]([C:23]([O:26][CH2:27][CH3:28])=[O:25])=[CH:6][CH:5]=1)=[O:15])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 24819Phosphorus pentachlorideHCID 15388893HCID 15388893, compound

Product 1

HCID 20329820HCID 20329820, compoundYield 80%

Procedure

In 50 ml of ethyl acetate was dissolved 5 g of 5-nitro-1,2,3,4-tetrahydro-1-naphthoic acid. After addition of 4.6 g of phosphorus pentachloride to the resulting solution at room temperature, the mixture was stirred for 30 minutes. The precipitates were removed by filtration and the filtrate was freed from ethyl acetate by distillation under reduced pressure. The residue was dissolved in 100 ml of fresh ethyl acetate. To the solution were added, with cooling, 4.1 g of p-ethoxycarbonylphenol and 2.5 g of triethylamine. The mixture was stirred for 24 hours. The reaction mixture was washed with a cold 5% sodium hydroxide solution and freed from the solvent by distillation to obtain 7.2 g (80% yield) of oily p-ethoxycarbonylphenyl 5-nitro-1,2,3,4-tetrahydro-1-naphthoate.

Workup

  1. customThe precipitates were removed by filtration
  2. distillationthe filtrate was freed from ethyl acetate by distillation under reduced pressure
  3. dissolutionThe residue was dissolved in 100 ml of fresh ethyl acetate
  4. additionTo the solution were added
  5. temperaturewith cooling
  6. stirringThe mixture was stirred for 24 hours
  7. washThe reaction mixture was washed with a cold 5% sodium hydroxide solution
  8. distillationfreed from the solvent by distillation

Sources & evidence

ORD record
ord-6860d014a5234634ab8d8aeb02435b40
Source dataset
uspto-grants-1980_07
Patent number
US04214093

Reaction notes

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