Ethanol → 2-(Ethoxycarbonyl)-6-nitrobenzoic acid

HRID 653709

Reaction equation

HRID 653709 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:13]([OH:15])=[O:14])([O-:3])=[O:2].S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[C:13]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH2:21][CH3:22])=[O:8])([OH:15])=[O:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 690433-Nitrophthalic acid

Product 1

HCID 120189282-(Ethoxycarbonyl)-6-nitrobenzoic acidYield 74%

Procedure

A solution of 3-nitrophthalic acid (35 g) in ethanol (300 ml) containing conc. sulfuric acid (20 ml) was heated for 24 hours under reflux. The solvent was distilled off, and the residue was poured into ice-water (700 ml), which was extracted with ethyl acetate. The organic layer was washed with water, which was extracted with an aqueous solution of potassium carbonate. The aqueous layer was made acidic with hydrochloric acid, followed by extraction with methylene chloride. The organic layer was washed with water and dried. The solvent was distilled off to give a solid product (29 g, 74%), which was used in the subsequent reaction without purification.

Workup

  1. temperaturewas heated for 24 hours
  2. temperatureunder reflux
  3. distillationThe solvent was distilled off
  4. additionthe residue was poured into ice-water (700 ml), which
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with water, which
  7. extractionwas extracted with an aqueous solution of potassium carbonate
  8. extractionfollowed by extraction with methylene chloride
  9. washThe organic layer was washed with water
  10. customdried
  11. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-6c0f696732694d07bf881e6f3f1308d7
Source dataset
uspto-grants-1992_07
Patent number
US05128356

Linked notes

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