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

HRID 2078549Notes

Reaction equation

HRID 2078549 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-ebadb4c82d1b48058bbe59c6530171f6
Source dataset
uspto-grants-2011_04
Patent number
US07928239B2

Reaction notes

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