Sodium Hydroxide → 2-Methoxy-3-nitrobenzoic acid

HRID 351343Notes

Reaction equation

HRID 351343 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8]>CO>[CH3:3][O:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 590805Methyl 2-methoxy-3-nitrobenzoate

Product 1

HCID 120151952-Methoxy-3-nitrobenzoic acidYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1N Sodium hydroxide was added to a solution (50 ml) of methyl 2-methoxy-3-nitrobenzoate (4.96 g, 23.5 mmol) in methanol and the mixture was stirred at 50° C. for 2 hrs. Methanol was evaporated under reduced pressure and water was added. The aqueous layer was acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was recrystallized from hexane-ethyl acetate to give the title compound (4.37 g) as pale-yellow crystals. melting point: 224–226° C.

Workup

  1. customMethanol was evaporated under reduced pressure and water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-32a364d3ba2d434ca707fb8ad0c8b738
Source dataset
uspto-grants-2007_02
Patent number
US07183415B2

Reaction notes

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