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

HRID 1968085Notes

Reaction equation

HRID 1968085 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 78.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a conc. H2SO4 (90 mL) was added portionwise 5-chloro-2-methylbenzoic acid (13.2 g, 77.6 mmol) at −5-0° C. Then a mixture of conc. HNO3 (10.5 g, 1744 mmol) in conc. H2SO4 (15 mL) was added dropwise at −5-0° C. over a period of about 1.5 hr. After the addition, the mixture was stirred at this temperature for 2 hr. The mixture was poured into crashed ice with vigorous stirring and the precipitate was collected by filtration. The precipitate was dissolved in EtOAc, washed with brine, dried over anhydrous Na2SO4, and concentrated to give a crude title compound (13.2 g), which was used in the next step without further purification.

Workup

  1. additionwas added dropwise at −5-0° C. over a period of about 1.5 hr
  2. additionAfter the addition
  3. additionThe mixture was poured
  4. stirringwith vigorous stirring
  5. filtrationthe precipitate was collected by filtration
  6. dissolutionThe precipitate was dissolved in EtOAc
  7. washwashed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5bd8297ff8644f97b9cb8c196e00055f
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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