Methanol → Methyl 3,5-dinitrobenzoate

HRID 2071008Notes

Reaction equation

HRID 2071008 reaction equation
O=S(Cl)Cl.[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1)[C:11]([OH:13])=[O:12])([O-:7])=[O:6].[CH3:20]O>>[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1)[C:11]([O:13][CH3:20])=[O:12])([O-:7])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 74333,5-Dinitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 222067Methyl 3,5-dinitrobenzoateYield 99%

Procedure

SOCl2 (3.4 ml, 5.61 g, 47.1 mmol, 5 eq) was added dropwise to a stirred solution of 3,5-dinitrobenzoic acid (2.0 g, 9.43 mmol, 1 eq, Aldrich) in 20 ml anhydrous MeOH at 0° C. under Ar. The reaction was stirred at 0° C. to room temperature overnight. The solvent was removed in vacuo, and the residue was dissolved in EtOAc. The organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo yielding 2.12 g (9.38 mmol, 99% yield) of methyl 3,5-dinitrobenzoate.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1)
  4. dry with materialdried over Na2SO4
  5. filtrationThe inorganics were filtered off
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-479b10362ec74d36a808b8025a491b2d
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…