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

HRID 1106746Notes

Reaction equation

HRID 1106746 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. ##STR141##

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-3611756fad8b49a49979810baabdecf3
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

Loading…