4-Nitrophenol → Adipic acid p-nitrophenyl ester

HRID 1732975Notes

Reaction equation

HRID 1732975 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.[C:11]1(=[O:19])[O:18][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1>C(OCC)(=O)C>[N+:7]([C:6]1[CH:5]=[CH:4][C:3]([O:10][C:11](=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:2][CH:1]=1)([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 567658Adipic anhydride

Product 1

HCID 15926815Adipic acid p-nitrophenyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

28 g of finely powdered p-nitrophenol were added to 25.6 g of adipic anhydride and the mixture was stirred at room temperature overnight, whereupon the contents of the flask solidified. The mass was melted, whilst stirring, and the melt was dissolved in 350 ml of ethyl acetate. The solution was extracted several times with water and the ethyl acetate was distilled off in vacuo. The residue was recrystallised three times from acetonitrile. Yield: 45.2 g (85% of theory) of melting point 104°-105° C.

Workup

  1. stirringwhilst stirring
  2. extractionThe solution was extracted several times with water
  3. distillationthe ethyl acetate was distilled off in vacuo
  4. customThe residue was recrystallised three times from acetonitrile

Sources & evidence

ORD record
ord-229a33e6d9e344b19636aeb23f8a6348
Source dataset
uspto-grants-1980_12
Patent number
US04239902

Reaction notes

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