Sodium Hydroxide → 4-Cyano-3-methoxybenzoic acid

HRID 735741Notes

Reaction equation

HRID 735741 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][C:4]=1[O:13][CH3:14])#[N:2].[OH-].[Na+]>CO>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22464400Methyl 4-cyano-3-methoxybenzoate

Product 1

HCID 187797844-Cyano-3-methoxybenzoic acidYield 106.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (37 ml) of methyl 4-cyano-3-methoxybenzoate (700 mg, 3.66 mmol) in methanol was added 1M aqueous sodium hydroxide solution (37 ml), and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, the residue was dissolved in water, and the mixture was washed with diethyl ether. The aqueous layer was neutralized with 1M hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous MgSO4 and concentrated under reduced pressure to give the title compound (690 mg, ca. 100%) as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washthe mixture was washed with diethyl ether
  4. extractionextracted with dichloromethane
  5. dry with materialThe extract was dried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-841afae2839641e0a7979e26a81bbf6a
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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