Phosphorus pentachloride → HCID 20329754, compound

HRID 2058050Notes

Reaction equation

HRID 2058050 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)Cl>C(OCC)(=O)C>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[C:14]([O:16][C:4]2[CH:13]=[CH:12][CH:7]=[CH:6][CH:5]=2)=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 18922786HCID 18922786, compound

Product 1

HCID 20329754HCID 20329754, compoundYield 148.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 50 ml of ethyl acetate was dissolved 1.5 g of 7-nitro-1,2,3,4-tetrahydro-1-naphthoic acid. To the resulting solution was added at room temperature 1.3 g of phosphorus pentachloride, and the mixture was stirred for 30 minutes. The precipitates were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in 50 ml of fresh ethyl acetate. To the solution were added with cooling 1.0 g of phenol and 8.5 g of triethylamine. The resulting 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 1.5 g of phenyl 7-nitro-1,2,3,4-tetrahydro-1-naphthoate having a melting point of 83°-84° C.

Workup

  1. customThe precipitates were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 50 ml of fresh ethyl acetate
  4. additionTo the solution were added
  5. temperaturewith cooling 1.0 g of phenol and 8.5 g of triethylamine
  6. stirringThe resulting 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-69ca5d825b9d4896aae5c2d3021f6671
Source dataset
uspto-grants-1980_07
Patent number
US04214093

Reaction notes

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