Methanol → Methyl 2-chloro-5-nitrobenzoate

HRID 1363408Notes

Reaction equation

HRID 1363408 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:19]O>>[CH3:19][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[Cl:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 172872-Chloro-5-nitrobenzoic acid

Product 1

HCID 22754Methyl 2-chloro-5-nitrobenzoate

Procedure

2-Chloro-5-nitrobenzoic acid (11 g, 54.5 mmol) was dissolved in methanol (100 mL). Conc. H2SO4 (2 mL) was added slowly and the reaction mixture heated to reflux for 4 h. The mixture was concentrated and the residue was allowed to cool to room temperature. It was poured over crushed ice. The organic product was extracted using diethyl ether (2×200 mL). The organic extract was washed with water, 10% aqueous NaHCO3, dried (anhydrous Na2SO4) and concentrated to get the title compound.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 4 h
  3. concentrationThe mixture was concentrated
  4. additionIt was poured
  5. customover crushed ice
  6. extractionThe organic product was extracted
  7. extractionThe organic extract
  8. washwas washed with water, 10% aqueous NaHCO3
  9. dry with materialdried (anhydrous Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-acbdd1b48c914dd0bfec09cf4ec703ec
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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