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

HRID 618238Notes

Reaction equation

HRID 618238 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13].S(=O)(=O)(O)O>[N+](C)([O-])=O>[CH3:1][C:2]1[C:10]([N+:12]([O-:14])=[O:13])=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5]

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 6375NitromethaneSolvent

Procedure

2,6-Dimethylbenzoic acid (15 g) dissolved in 350 ml of nitromethane was cooled in an ice bath and treated with 18.9 ml of 70% nitric acid and then 14 ml of concentrated sulfuric acid. The bath was removed and the mixture was stirred at room temperature for 22 hr. The mixture was poured into ethyl acetate, washed several times with water, dried, evaporated, and 17.2 g of 2,6-dimethyl-3-nitrobenzoic acid, mp 115.9-116.5° C., was obtained. ##STR123##

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe bath was removed
  3. additionThe mixture was poured into ethyl acetate
  4. washwashed several times with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-61b4552382ff4e5eac4750615201e5a9
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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