Nitric Acid → 5-Chloro-2-methyl-3-nitrobenzoic acid

HRID 2208950Notes

Reaction equation

HRID 2208950 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 820095-Chloro-2-methylbenzoic acid

Product 1

HCID 230097625-Chloro-2-methyl-3-nitrobenzoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a stirred solution of 5-chloro-2-methylbenzoic acid (4.0 g, 24 mmol) in concentrated H2SO4 (27 mL) at −10° C. was added a nitrating solution comprised of concentrated HNO3 (3.3 g, 53 mmol) dissolved in concentrated H2SO4 (4.4 mL). The resulting mixture was stirred at −10° C. for 3 h and poured onto ice water. The resulting precipitate was filtered, washed with water and dried under vacuum to give the title compound (4.95 g, 99%).

Workup

  1. additionpoured onto ice water
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-0f7e67fe178a4cff81cbbb35d28844b0
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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