Nitric Acid → 2,6-Dimethyl-3-nitrobenzoic acid

HRID 485540

Reaction equation

HRID 485540 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH3:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:12]=1[C:13]([OH:15])=[O:14]>C(Cl)Cl>[CH3:10][C:11]1[C:19]([N+:6]([O-:9])=[O:7])=[CH:18][CH:17]=[C:16]([CH3:20])[C:12]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 124392,6-Dimethylbenzoic acid

Product 1

HCID 2393292,6-Dimethyl-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 46 ml of concentrated sulfuric acid and 23.5 ml of concentrated nitric acid was added slowly to a stirred solution of 2,6-dimethylbenzoic acid (50.0 g, 0.333 mole) in 200 ml of methylene chloride at a rate such that a gentle reflux was maintained throughout the addition. After complete addition, reflux was maintained for 30 minutes. The reaction mixture was cooled, poured onto 300 g of ice and the organic phase separated. The aqueous phase was extracted with three 200 ml portions of diethyl ether, and the organic phases were combined, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed from the filtrate under reduced pressure to give 2,6-dimethyl-3-nitrobenzoic acid (60.2 g) as a solid.

Workup

  1. temperaturea gentle reflux
  2. temperaturewas maintained throughout the addition
  3. additionAfter complete addition
  4. temperaturereflux
  5. temperaturewas maintained for 30 minutes
  6. temperatureThe reaction mixture was cooled
  7. customthe organic phase separated
  8. extractionThe aqueous phase was extracted with three 200 ml portions of diethyl ether
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-54fe3c46726b4aaca4c32bb2c93a68f1
Source dataset
uspto-grants-1985_08
Patent number
US04536591

Linked notes

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