Nitric Acid → 4-Nitro-2,3,6-trimethylanisole

HRID 439867Notes

Reaction equation

HRID 439867 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[O:10][CH3:11].[N+:12]([O-])([OH:14])=[O:13]>C(O)(=O)C>[N+:12]([C:6]1[CH:5]=[C:4]([CH3:9])[C:3]([O:10][CH3:11])=[C:2]([CH3:1])[C:7]=1[CH3:8])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 5916042-Methoxy-1,3,4-trimethylbenzene

Product 1

HCID 224085124-Nitro-2,3,6-trimethylanisoleYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred, heated (70°-80° C.) solution of 20.3 g (0.135 mol) of 2,3,6-trimethylanisole in 200 ml of acetic acid was added dropwise 9.65 ml of conc. aqueous HNO3 in 20 ml of acetic acid. After the addition the mixture was poured onto ice, and the resulting mixture was extracted 3 times with methylene chloride. The organic phase was evaporated to remove acetic acid and methylene chloride, and the residue was dissolved in ether and washed twice with NaOH-solution and twice with NaHCO3 -solution. Drying (MgSO4) and evaporation gave 19.0 g (72%) of the product, which was used without further purification in the next step.

Workup

  1. additionAfter the addition the mixture
  2. additionwas poured onto ice
  3. extractionthe resulting mixture was extracted 3 times with methylene chloride
  4. customThe organic phase was evaporated
  5. customto remove acetic acid and methylene chloride
  6. dissolutionthe residue was dissolved in ether
  7. washwashed twice with NaOH-solution and twice with NaHCO3 -solution
  8. customDrying
  9. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-9678d136b6a5425fb84ba0c4d1a38781
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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