Nitric Acid → HCID 59761726, compound

HRID 2401457Notes

Reaction equation

HRID 2401457 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[N+:19]([O-])([OH:21])=[O:20]>>[CH3:6][C:7]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[C:13]([N+:19]([O-:21])=[O:20])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 747904-Nitro-o-toluic acid

Product 1

HCID 59761726HCID 59761726, compoundYield 85%

Conditions

Temperature
0 °C

Procedure

To concentrated sulfuric acid (10 mL) at 0° C. was added concentrated nitric acid (10 mL) dropwise and the mixture was allowed to stir at 0° C. for 10 min. 2-Methyl-4-nitrobenzic acid (1.81 g, 10 mmol) was added and the mixture was allowed to stir at RT for 5 d. The mixture was poured into ice-cold water and the solid was removed by filtration and dried to give 2-methyl-4,5-dinitrobenzoic acid (1.93 g, 85%) as an off-white solid. LCMS (10 cm_ESCI_Formic_MeCN): [M−H]−=225 at 3.10 min. 1H NMR (400 MHz, d6-DMSO): δ 8.53 (s, 1H), 8.26 (s, 1H), 2.71 (s, 3H).

Workup

  1. stirringto stir at RT for 5 d
  2. additionThe mixture was poured into ice-cold water
  3. customthe solid was removed by filtration
  4. customdried

Sources & evidence

ORD record
ord-f7e0a5ed6d49471bb2649bd3abb8049d
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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