Ethyl Acetate → 1,5-Dimethoxy-2,4-dinitrobenzene

HRID 1285267Notes

Reaction equation

HRID 1285267 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][O-:16].[Na+].[C:18](OCC)(=[O:20])C>CO>[CH3:18][O:20][C:2]1[CH:7]=[C:6]([O:16][CH3:15])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 772861,3-Dichloro-4,6-dinitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 6150531,5-Dimethoxy-2,4-dinitrobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 20.0 g (0.084 moles) 1,5-dichloro-2,4-dinitrobenzene in 200 ml methanol is added 22.7 g (0.42 moles) sodium methoxide. The mixture is heated to reflux and the reaction is monitored by TLC (ethyl acetate). TLC after approximately 12 hours shows the reaction is complete. The host mixture is poured into 750 ml ice/H2O. The pale yellow precipitate is collected by vacuum filtration and dried in the vacuum oven at 50° C. Yield is 16.3 g (85.7%). Recrystallization using toluene and 1 g decolorizing charcoal yields 11.5 g product, m.p. 153°-155° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. filtrationThe pale yellow precipitate is collected by vacuum filtration
  4. customdried in the vacuum oven at 50° C
  5. customRecrystallization

Sources & evidence

ORD record
ord-98ac8f8646be4fc397764259d288cfbc
Source dataset
uspto-grants-1986_01
Patent number
US04566876

Reaction notes

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