Methanol → Methyl 2-chloro-3-nitrobenzoate

HRID 1639839Notes

Reaction equation

HRID 1639839 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:19]O>>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 198702-Chloro-3-nitrobenzoic acid

Product 1

HCID 10751184Methyl 2-chloro-3-nitrobenzoateYield 99%

Procedure

A mixture of 2-chloro-3-nitrobenzoic acid (24.8 g, 123 mmol) and sulfuric acid (3.00 mL, 38.2 mmol) in methanol (400 mL) was stirred at. 80° C. for 12 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate. This mixture was washed with 10% aqueous sodium hydroxide solution, water and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (26.5 g, yield 99%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThis mixture was washed with 10% aqueous sodium hydroxide solution, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9a178dd661f14ec5bcb47a7272f58e47
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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