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

HRID 277459

Reaction equation

HRID 277459 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 acid

Procedure

A mixture of 3-nitrophthalic acid (35 g) in ethanol (300 ml) containing conc. sulfuric acid (20 ml) was heated under reflux for 24 hours. The solvent was evaporated in vacuo and the residue was poured into cold water (700 ml). The mixture was extracted with ethyl acetate. The organic layer was washed with water and shaken with an aqueous solution of potassium carbonate. The aqueous layer was made acidic with hydrochloric acid and the mixture was extracted with methylene chloride. The organic layer was washed with water, then dried, followed by evaporation of the solvent. The resultant solid (29 g, 74%) was used for the subsequent reaction without purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customThe solvent was evaporated in vacuo
  4. additionthe residue was poured into cold water (700 ml)
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. extractionthe mixture was extracted with methylene chloride
  8. washThe organic layer was washed with water
  9. customdried
  10. customfollowed by evaporation of the solvent
  11. customThe resultant solid (29 g, 74%) was used for the subsequent reaction without purification

Sources & evidence

ORD record
ord-77067ba2db9644f991014130a3aa3f6b
Source dataset
uspto-grants-2002_03
Patent number
US06355808B2

Linked notes

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