Methanol → 2,4-Dimethoxy-1-nitrobenzene

HRID 1167632Notes

Reaction equation

HRID 1167632 reaction equation
[CH3:1][O-:2].[Na+].[Na].Cl[C:6]1[CH:11]=[C:10](Cl)[CH:9]=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14].[CH3:16][OH:17]>>[CH3:1][O:2][C:6]1[CH:11]=[C:10]([O:17][CH3:16])[CH:9]=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 4

HCID 887Methanol3×HCID 118992,4-DichloronitrobenzeneHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 786332,4-Dimethoxy-1-nitrobenzene

Procedure

To a solution of sodium methoxide in methanol (freshly prepared by adding 50.0 g (2.17 mol) of sodium, in portions, to 1.5 l of methanol at 0° C.) was added 2,4-dichloro-nitrobenzene (95.0 g, 0.495 mol) in methanol (100 ml). After refluxing for 3 days, the reaction mixture was cooled in an ice bath and filtered, the precipitate was washed with water and dried (Na2SO4). The title compound was collected as a yellow solid (83.0 g, 91%).

Workup

  1. temperatureAfter refluxing for 3 days
  2. temperaturethe reaction mixture was cooled in an ice bath
  3. filtrationfiltered
  4. washthe precipitate was washed with water
  5. dry with materialdried (Na2SO4)
  6. customThe title compound was collected as a yellow solid (83.0 g, 91%)

Sources & evidence

ORD record
ord-a432d330f4834904818ea167460f4bf1
Source dataset
uspto-grants-2003_09
Patent number
US06620826B2

Reaction notes

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