Water → 2-Methoxy-5-(4-nitrophenoxy)benzoic acid

HRID 598437Notes

Reaction equation

HRID 598437 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:4].[OH-].[K+].O>CO>[C:3]([C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 230230954-(3-Methoxycarbonyl-4-methoxyphenoxy)-1-nitrobenzene

Product 1

HCID 230230632-Methoxy-5-(4-nitrophenoxy)benzoic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(3-methoxycarbonyl-4-methoxyphenoxy)-1-nitrobenzene (1.2 g), KOH (0.33 g) and water (5 mL) in MeOH (45 mL) was stirred at room temp. overnight and then heated at the reflux temp. for 4 h. The resulting mixture was cooled to room temp. and concentrated under reduced pressure. The residue was dissolved in water (50 mL), and the aqueous mixture was made acidic with a 1N HCl solution. The resulting mixture was extracted with EtOAc (50 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to give 4-(3-carboxy-4-methoxyphenoxy)-1-nitrobenzene (1.04 g).

Workup

  1. temperatureheated at the reflux temp
  2. waitfor 4 h
  3. temperatureThe resulting mixture was cooled to room temp.
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in water (50 mL)
  6. extractionThe resulting mixture was extracted with EtOAc (50 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-86a2916fb9114c2aac2b1c53f972024a
Source dataset
uspto-grants-2011_03
Patent number
US07897623B2

Reaction notes

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