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

HRID 2354350Notes

Reaction equation

HRID 2354350 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-6f213d45c25d4af2beb3c168f271ce53
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

Loading…