Nitric Acid → 4-Methyl-3-nitrobenzoic acid

HRID 1808321Notes

Reaction equation

HRID 1808321 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH3:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1>>[CH3:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]=1[N+:6]([O-:9])=[O:7]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 7470P-Toluic Acid

Product 1

HCID 73194-Methyl-3-nitrobenzoic acidYield 82.7%

Conditions

Temperature
0 °C

Procedure

Conc. sulfuric acid (25 ml; 0.5 equiv.) was added over a period of 10 minutes to nitric acid at 0° C. (69-72%; 25 ml; 0.5 equiv.). The resulting mixture was stirred for 30 minutes at 0° C. Conc. sulfuric acid (75 ml; 1.5 equiv.) was added at room temperature, over a period of 20 minutes, to 4-methylbenzoic acid (50 g; 1 equiv.). The resulting suspension was cooled to 0° C., and the nitrating acid was added thereto over a period of 45 minutes. The resulting reaction mixture was stirred for 1 hour at 10-20° C. When the conversion was complete, the reaction mixture was poured onto ice-water and the resulting white solid was filtered out and dried. 4-Methyl-3-nitrobenzoic acid (66.5 g; 82.7%) was obtained in the form of a white solid.

Workup

  1. temperatureThe resulting suspension was cooled to 0° C.
  2. additionthe nitrating acid was added
  3. waitover a period of 45 minutes
  4. customThe resulting reaction mixture
  5. stirringwas stirred for 1 hour at 10-20° C
  6. additionthe reaction mixture was poured onto ice-water
  7. filtrationthe resulting white solid was filtered out
  8. customdried

Sources & evidence

ORD record
ord-597cc087960b420e97167f763367418f
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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