Nitric Acid → 4-Ethyl-3-nitrobenzoic acid

HRID 1072843Notes

Reaction equation

HRID 1072843 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]>>[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])[CH3:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 120864-Ethylbenzoic Acid

Product 1

HCID 81670864-Ethyl-3-nitrobenzoic acidYield 94.8%

Conditions

Temperature
4.5 °C

Procedure

4-Ethylbenzoic acid (20 g, 133 mmol) was ice-cooled and fuming nitric acid (94%, d=1.50, 50 ml) was dropwise added thereto for 40 min. The mixture was stirred at 4-5° C. for 1.25 hr. The resulting yellow suspension was poured into ice-water and the precipitated crystals were collected by filtration. The crystals were dissolved in ethanol, and water was added for recrystallization to give the objective compound (24.6 g, 94.8%) as colorless crystals.

Workup

  1. temperaturecooled
  2. filtrationthe precipitated crystals were collected by filtration
  3. dissolutionThe crystals were dissolved in ethanol
  4. additionwater was added for recrystallization

Sources & evidence

ORD record
ord-1331128ebe094f018cb9c9a4c9071bc9
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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