Nitric Acid → 2,6-Dimethoxy-3-nitrotoluene

HRID 322010Notes

Reaction equation

HRID 322010 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH3:11].[N+:12]([O-])([OH:14])=[O:13]>>[CH3:10][O:9][C:5]1[C:6]([N+:12]([O-:14])=[O:13])=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[CH3:11]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 797552,6-Dimethoxytoluene

Product 1

HCID 121663502,6-Dimethoxy-3-nitrotoluene

Conditions

Temperature
0 °C

Procedure

11.62 g (76.45 mmol) of 2,6-dimethoxytoluene were introduced in portions into 40 ml of concentrated nitric acid cooled to 0° C. After stirring at 0° C. for 15 min, the reaction solution was poured onto 250 ml of ice and extracted 3× with EA. The combined EA extracts were dried over Na2SO4, the solvent was removed in vacuo, and the brown oily residue was purified by means of column chromatography on SiO2 (EA/heptane 1:8). 8.59 g of the title compound were isolated in the form of a red oil.

Workup

  1. extractionextracted 3× with EA
  2. dry with materialThe combined EA extracts were dried over Na2SO4
  3. customthe solvent was removed in vacuo
  4. customthe brown oily residue was purified by means of column chromatography on SiO2 (EA/heptane 1:8)

Sources & evidence

ORD record
ord-358b2c75318f48dbadf291e8506f41e1
Source dataset
uspto-grants-2001_04
Patent number
US06211196B1

Reaction notes

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