Methanol → Methyl 4-methoxy-3,5-dinitrobenzoate

HRID 852534Notes

Reaction equation

HRID 852534 reaction equation
[CH3:1][O:2][C:3]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:15]([O-:17])=[O:16].OS(O)(=O)=O.[CH3:23]O>>[CH3:23][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:3]([O:2][CH3:1])=[C:4]([N+:15]([O-:17])=[O:16])[CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2916454-Methoxy-3,5-dinitrobenzoic acid

Product 1

HCID 14091421Methyl 4-methoxy-3,5-dinitrobenzoateYield 65%

Procedure

To a solution of crude 4-methoxy-3,5-dinitro-benzoic acid (D24) (4.43 g, 17.3 mmol, 1 equiv) in MeOH (60 ml) was added concentrated H2SO4 (4 ml). The resulting mixture was refluxed for 3 h, cooled to room temperature and concentrated in vacuo. The residue was partitioned between H2O and AcOEt. The two layers were separated and the organic phase was washed with saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (iso-hexane/AcOEt: 85/15) gave 4-methoxy-3,5-dinitro-benzoic acid methyl ester (D25) (2.84 g, 65%) as an off white solid.

Workup

  1. temperatureThe resulting mixture was refluxed for 3 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between H2O and AcOEt
  4. customThe two layers were separated
  5. washthe organic phase was washed with saturated aqueous NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel (iso-hexane/AcOEt: 85/15)

Sources & evidence

ORD record
ord-731d9c51fccb4787b83a047d14979c41
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

Loading…