Nitric Acid → 4-Ethyl-3-nitrobenzoic acid

HRID 1859659Notes

Reaction equation

HRID 1859659 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[CH3:2].[N+:12]([O-])([OH:14])=[O:13]>O>[N+:12]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:3]=1[CH2:1][CH3:2])[C:7]([OH:9])=[O:8])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 120864-Ethylbenzoic Acid

Product 1

HCID 81670864-Ethyl-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Ethylbenzoic acid (12.0 g, 79.9 mmol) was added portionwise to fuming nitric acid (62 mL) with stirring at room temperature. Following the addition, the mixture was poured into water (500 mL), stirred, and extracted with ethyl acetate (300 mL). Saturated brine (150 mL) was added and the mixture shaken then separated. The organic solution was washed with brine then dried over magnesium sulfate. Filtration, removal of the solvent by rotovap under reduced pressure, and trituration of the residue in hexane afforded the product (13.3 g); pure after recrystallization from hexane/ethyl acetate.

Workup

  1. additionthe addition
  2. stirringstirred
  3. extractionextracted with ethyl acetate (300 mL)
  4. additionSaturated brine (150 mL) was added
  5. stirringthe mixture shaken
  6. customthen separated
  7. washThe organic solution was washed with brine
  8. dry with materialthen dried over magnesium sulfate
  9. filtrationFiltration, removal of the solvent by rotovap under reduced pressure, and trituration of the residue in hexane

Sources & evidence

ORD record
ord-17b3e85a59004f6997653f0c0673c4ae
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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