Sodium Hydroxide → (3-Methoxy-4-nitrophenyl)acetic acid

HRID 1503845Notes

Reaction equation

HRID 1503845 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12](C(OCC)=O)[C:13]([O:15]CC)=[O:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70559053HCID 70559053, compound

Product 1

HCID 16755859(3-Methoxy-4-nitrophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the product of EXAMPLE 30A (0.3 g, 0.96 mmol) in ethanol (2 mL) was added 2N aqueous sodium hydroxide (2 mL) and the mixture was stirred at room temperature for 12 hours. Ater concentration, the residue was diluted with water and extracted with ethyl acetate. The aqueous phase was acidified to pH 2-3 with concentrated HCl and extracted with ethyl acetate (3×5 mL). The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The title compound was used in the next step without further purification.

Workup

  1. concentrationAter concentration
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe title compound was used in the next step without further purification

Sources & evidence

ORD record
ord-f248bbfd396748dbbdabee65ecda519f
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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