Nitric Acid → 2,4,6-Trimethyl-3-nitrobenzoic acid

HRID 987846Notes

Reaction equation

HRID 987846 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].[N+:13]([O-])([OH:15])=[O:14]>>[N+:13]([C:10]1[C:2]([CH3:1])=[C:3]([C:7]([CH3:12])=[CH:8][C:9]=1[CH3:11])[C:4]([OH:6])=[O:5])([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 101942,4,6-Trimethylbenzoic acid

Product 1

HCID 81670772,4,6-Trimethyl-3-nitrobenzoic acidYield 94%

Procedure

To a suspension of 2,4,6-trimethylbenzoic acid (4.6 g, 28 mmol) in 70% HNO3 (85 mL) conc. H2SO4 (5 mL). was added dropwise at RT. The brown reaction mixture was stirred for 1 h, poured into ice-water (500 mL). The product was extracted into ethyl acetate, the extract was washed with water, dried over MgSO4 and concentrated to give 3-nitro-2,4,6-trimethylbenzoic acid as a yellow solid (6.7 g, 94%).

Workup

  1. additionwas added dropwise at RT
  2. extractionThe product was extracted into ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5bbccd3583664f3b86f56fdba47345ce
Source dataset
uspto-grants-2003_10
Patent number
US06632829B2

Reaction notes

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