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

HRID 2114354

Reaction equation

HRID 2114354 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[O:10][CH3:11].[N+:12]([O-])([OH:14])=[O:13]>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 905522,5-Dimethoxytoluene

Product 1

HCID 27780951,4-Dimethoxy-2-methyl-5-nitrobenzeneYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
40 °C

Procedure

2-Methyl-1,4-bis(methyloxy)benzene (6.12 g, 40 mmol) was dissolved in acetic acid (20 mL) and heated at 40° C. A solution of nitric acid (4.32 g) in acetic acid (10 mL) was added to above solution drop wise over 5 minutes. The reaction mixture was stirred at 40° C. for 30 min (yellow precipitates formed), then room temperature for 30 min and then diluted with water (300 mL). The precipitate was collected by filtration, washed with water, and dried in the air for 16 h to afford the title compound (7.56 g, 96%) as a yellow solid. MS (ES) m/e 198 [M+H]+.

Workup

  1. custom(yellow precipitates formed)
  2. waitroom temperature for 30 min
  3. additiondiluted with water (300 mL)
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried in the air for 16 h

Sources & evidence

ORD record
ord-e0f63a35e0e4449c8d059001b5d17342
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Linked notes

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