Hydrochloric Acid → 4-Methoxy-3-nitrophenol

HRID 502748Notes

Reaction equation

HRID 502748 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](CC([O-])=O)=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14].[O-:16]CC.[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:16])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 70484552-(4-Methoxy-3-nitrophenyl)acetate

Product 1

HCID 149589074-Methoxy-3-nitrophenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methoxy-3-nitrophenylacetate (2.46 g, 11.7 mmol) was dissolved in anhydrous ethanol (80 ml) and sodium ethoxide (1.19 g, 17.5 mmol) was added. The reaction was stirred at room temperature for 0.5 h. The dark red solution was acidified with 2M HCl and concentrated under reduced pressure. The residue was taken up into water and extracted with dichloromethane. The combined organics were washed with 2M HCl and brine, then dried over sodium sulfate. Evaporation of the solvent under reduced pressure gave the title compound as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with dichloromethane
  3. washThe combined organics were washed with 2M HCl and brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8f04ea8b92bf4179a9e4cff06f4513de
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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