3,5-Dinitrobenzoic acid → Methyl 3,5-dinitrobenzoate

HRID 1370510Notes

Reaction equation

HRID 1370510 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].O=S(Cl)Cl.[CH2:20](N(CC)CC)C>>[CH3:20][O:8][C:7](=[O:9])[C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=1

Participants

4

Reactant 3

HCID 74333,5-Dinitrobenzoic acidHCID 8471TriethylamineHCID 24386Thionyl Chloride

Product 1

HCID 222067Methyl 3,5-dinitrobenzoateYield 97.3%

Procedure

To 3,5-Dinitro-benzoic Acid (Aldrich, 21.2 g, 100 mmol) was added SOCl2. The mixture was refluxed overnight. The excess SOCl2 was removed under reduced pressure. The residue was dissolved in 100 mL of MeOH, cooled in ice bath, and triethylamine (Aldrich, 21 mL, 150 mmol) was added slowly added. After the mixture was stirred at ambient temperature for 3 h, solvent was removed under reduced pressure. The residue was diluted with EtOAc and 1N HCl. The mixture was extracted 3× with EtOAc (100 mL). The organic layers were washed twice with a brine solution (100 mL), dried over Na2SO4. Removal of the solvent gave 22.0 g (97%) of product, which was pure enough for the next reaction.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe excess SOCl2 was removed under reduced pressure
  3. dissolutionThe residue was dissolved in 100 mL of MeOH
  4. temperaturecooled in ice bath
  5. additionadded
  6. customsolvent was removed under reduced pressure
  7. additionThe residue was diluted with EtOAc and 1N HCl
  8. extractionThe mixture was extracted 3× with EtOAc (100 mL)
  9. washThe organic layers were washed twice with a brine solution (100 mL)
  10. dry with materialdried over Na2SO4
  11. customRemoval of the solvent

Sources & evidence

ORD record
ord-f3427f9e172d4594a7ef67c675057c18
Source dataset
uspto-grants-2003_06
Patent number
US06583157B2

Reaction notes

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