Methanol → Methyl 2-chloro-3-nitrobenzoate

HRID 2061122Notes

Reaction equation

HRID 2061122 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:19]O>>[CH3:19][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[C:15]([N+:16]([O-:18])=[O:17])[C:7]=1[Cl:6]

Participants

4

Reactant 3

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

Product 1

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

Procedure

Concentrated sulfuric acid (2.0 mL) was added to a solution of 2-chloro-3-nitrobenzoic acid (10.0 g, 49.6 mmol) in methanol (80 mL), and the mixture was stirred under reflux overnight. After removing methanol by vacuum concentration, water was added, and extraction was performed with ethyl acetate. The organic extract was washed in series with water, saturated sodium hydrogen carbonate and saturated saline, and dried over magnesium sulfate. The title compound (10.6 g, 99%) was obtained by vacuum concentration as a white solid.

Workup

  1. temperatureunder reflux overnight
  2. customAfter removing methanol
  3. concentrationby vacuum concentration, water
  4. additionwas added
  5. extractionextraction
  6. extractionThe organic extract
  7. washwas washed in series with water, saturated sodium hydrogen carbonate and saturated saline
  8. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-4b5ede88470a4837862b1e48927d50da
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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