Potassium Carbonate → 2-Methoxy-1,3-dimethyl-5-nitrobenzene

HRID 2103077

Reaction equation

HRID 2103077 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([CH3:12])[C:3]=1N.[C:13]([O-])([O-])=[O:14].[K+].[K+]>CC(C)=O>[CH3:13][O:14][C:3]1[C:2]([CH3:1])=[CH:8][C:7]([N+:9]([O-:11])=[O:10])=[CH:6][C:5]=1[CH3:12]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 281592,6-Dimethyl-4-nitroaniline

Product 1

HCID 1398352-Methoxy-1,3-dimethyl-5-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,6-Dimethyl-4-nitroaniline (15 g) Me2SO4 (22 g) and K2CO3 (23 g) were dissolved in 150 mL acetone and refluxed for 3 hours. The reaction mixture was filtered and concentrated. The organic residue was dissolved in warm hexane and let to crystallize out in the fridge. After filtration, 2-methoxy-1,3-dimethyl-5-nitrobenzene was collected as white solid (12 g). 1H-NMR (300 MHz, CDCl3): δ=7.95 (s, 2H), 3.80 (s, 3H), 2.38 (s, 6H) ppm. MS: m/z 182 (100, M+H)+

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. dissolutionThe organic residue was dissolved in warm hexane
  5. customto crystallize out in the fridge
  6. filtrationAfter filtration, 2-methoxy-1,3-dimethyl-5-nitrobenzene
  7. customwas collected as white solid (12 g)

Sources & evidence

ORD record
ord-46f2f9b562a248c5a445211dd4f33047
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Linked notes

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