1-Chloro-2,6-dinitrobenzene → 2,6-Dinitrophenyl methyl ether

HRID 131077

Reaction equation

HRID 131077 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][O-:15].[Na+]>CO.O>[N+:11]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[O:15][CH3:14])([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 118141-Chloro-2,6-dinitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 5977192,6-Dinitrophenyl methyl etherYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

0.200 g (1.00 mmol) of commercially available 2-chloro-1,3-dinitrobenzene was dissolved in a warm solution of 15 ml methanol and 0.223 g (4.13 mmol) of NaOMe. The reaction was stirred overnight with continued warming. The residue was dissolved in water after evaporation of the solvent. The aqueous solution was extracted with dichloromethane, dried and evaporated under reduced pressure to give 0.187 g of 2,6-dinitroanisole (95%) as yellow flakes. 1H NMR (CDCl3) δ 8.06 (d, J=8.2 Hz, 2H, Ar—H), 7.38 (t, J=8.2 Hz, 1H, Ar—H), 4.09 (s, 3H, O—CH3). 13C NMR (CDCl3) δ 148.0, 129.4, 124.2, 65.1.

Workup

  1. customafter evaporation of the solvent
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. customdried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2ffdd6d00beb4a21b22b9ccbca05892f
Source dataset
uspto-grants-2008_06
Patent number
US07384789B2

Linked notes

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