Hydrochloric Acid → 3-Methoxy-4-nitrophenol

HRID 502753Notes

Reaction equation

HRID 502753 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.Cl.[OH-:14].[K+]>>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([OH:14])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 129005323-Methoxy-4-nitrophenol

Conditions

Temperature
90 °C

Procedure

4-Fluoro-2-methoxynitrobenzene (4.68 g, 27.4 mmol) was suspended in a 5M potassium hydroxide solution (50 ml) and heated to 90° C. for 5 h. The red solution was cooled to room temperature and acidified to pH 6 with 1M HCl. The aqueous solution was extracted three times with ethyl acetate and the combined organics were washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure, followed by purification by flash column chromatography (1:1 hexane/ethyl acetate) afforded the title compound as a yellow solid.

Workup

  1. temperatureThe red solution was cooled to room temperature
  2. extractionThe aqueous solution was extracted three times with ethyl acetate
  3. washthe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. customfollowed by purification by flash column chromatography (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8c2c52f09e224edcaf3f08e76b1d461c
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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