Nitric Acid → 2-Methoxy-4-methyl-5-nitrobenzoic acid

HRID 2293525

Reaction equation

HRID 2293525 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH3:12])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 5971642-Methoxy-4-methylbenzoic acid

Product 1

HCID 214770512-Methoxy-4-methyl-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A 2.00 g portion of 2-methoxy-4-methylbenzoic acid was dissolved in 10 ml of sulfuric acid. With stirring at 0° C., 0.88 ml of concentrated nitric acid was added thereto dropwise. After 4 hours of stirring at room temperature, and ice water was added. The thus formed crystals were collected by filtration, dried under a reduced pressure and then purified by column chromatography (chloroform:methanol=30:1) to give 1.32 g of 2-methoxy-4-methyl-5-nitrobenzoic acid as yellow crystals.

Workup

  1. stirringAfter 4 hours of stirring at room temperature
  2. filtrationThe thus formed crystals were collected by filtration
  3. customdried under a reduced pressure
  4. custompurified by column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-87f4a387079241a9818c7c708286625e
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Linked notes

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