Sodium Hydroxide → 3-Methoxy-4-nitrophenol

HRID 1699130Notes

Reaction equation

HRID 1699130 reaction equation
[OH-:1].[Na+].F[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([O:13][CH3:14])[CH:5]=1>CS(C)=O.O>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([OH:1])=[CH:5][C:6]=1[O:13][CH3:14])([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 129005323-Methoxy-4-nitrophenol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide was added to a stirred solution of 4-fluoro-2-methoxynitrobenzene (11.1 g.) in DMSO (60 ml.) at ambient temperature and the mixture was heated at 85 degC. for 2.5 hr. The cooled solution was diluted with water (100 ml.) and extracted with ether (3×100 ml.) The combined ethereal solution was extracted with 2n NaOH (3×75 ml.) and the combined aqueous phase brought to pH 2 by the addition of 2N HCl. The precipitated product was collected and washed with water. The product was dried over phosphorous pentoxide. Yield 7.4 g. m/Z 170.1(M+H). It was used without further purification in the next step (cf Example 1c).

Workup

  1. temperaturethe mixture was heated at 85 degC
  2. extractionextracted with ether (3×100 ml.) The combined ethereal solution
  3. extractionwas extracted with 2n NaOH (3×75 ml.)
  4. additionthe combined aqueous phase brought to pH 2 by the addition of 2N HCl
  5. customThe precipitated product was collected
  6. washwashed with water
  7. dry with materialThe product was dried over phosphorous pentoxide
  8. customIt was used without further purification in the next step (cf Example 1c)

Sources & evidence

ORD record
ord-ba72ac1f5b244a24a3f5d6ad0a8cbabf
Source dataset
uspto-grants-2002_02
Patent number
US06344570B1

Reaction notes

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