Nitric Acid → HCID 89619360, compound

HRID 1502056Notes

Reaction equation

HRID 1502056 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[N+:13]([O-])([OH:15])=[O:14]>>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:13]([O-:15])=[O:14])=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 785542-Methyl-3-nitroanisole

Product 1

HCID 89619360HCID 89619360, compound

Procedure

To cooled (0° C.) fuming nitric acid (100 mL) was added slowly 2-methyl-3-nitroanisole (13.0 g, 77.8 mmol) in ten times. After the addition, the mixture was warmed to r.t. and stirred for 4 h, then poured into ice-water (500 g). The resulting mixture was extracted with EtOAc (3×500 mL). The combined organic layers were washed with water, saturated NaHCO3, brine, dried over Na2SO4, and concentrated to dryness. The residue was purified by silica column chromatography (petroleum ether/EtOAc=20:1) to obtain the pure product 1-methoxy-2-methyl-3,4-dinitrobenzene.

Workup

  1. additionAfter the addition
  2. extractionThe resulting mixture was extracted with EtOAc (3×500 mL)
  3. washThe combined organic layers were washed with water, saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by silica column chromatography (petroleum ether/EtOAc=20:1)

Sources & evidence

ORD record
ord-b1b58fab25234bcba51bc4c5418ed317
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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