Nitric Acid → 1,4-Dimethoxy-2-methyl-5-nitrobenzene

HRID 337363

Reaction equation

HRID 337363 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH3:11].[N+:12]([O-])([OH:14])=[O:13]>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:12]([O-:14])=[O:13])[C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH3:11]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 905522,5-Dimethoxytoluene

Product 1

HCID 27780951,4-Dimethoxy-2-methyl-5-nitrobenzeneYield 96.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

2,5-dimethoxy toluene (6.0 g) was dissolved in acetic acid (20 mL). To the solution, a solution of fuming nitric acid (d=1.50, 4.32 g) in acetic acid (10 mL) was added dropwise at 40° C. over a period of 5 min. The mixture was stirred at 40° C. for 30 min. The reaction mixture was then allowed to cool to room temperature, which was stirred for another 30 min. Then the reaction mixture was diluted with cold water (300 mL). The resulting precipitate was filtered washed with cold water (100 mL) and dried under reduced pressure to afford the title compound (7.5 g).

Workup

  1. temperatureto cool to room temperature
  2. stirringwhich was stirred for another 30 min
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with cold water (100 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-deeb7964a5b44e7e8abe2dea31a57b0e
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Linked notes

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