4-Methoxyphenol → p-(p-Nitrophenoxy)anisole

HRID 1591005Notes

Reaction equation

HRID 1591005 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:16]([OH:17])=[CH:15][CH:14]=1.[OH-].[K+]>[Cu]>[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:16]([O:17][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 114661-Bromo-4-nitrobenzeneHCID 14797Potassium Hydroxide

Product 1

HCID 80637p-(p-Nitrophenoxy)anisoleYield 30.9%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

4-Bromonitrobenzene (4.0 g), hydroquinone monomethyl ether (3.1 g), potassium hydroxide (1.5 g) and copper powder (0.1 g) were mixed and the reaction was carried out at 160° C. to 200° C. for 3 hours. After cooling to room temperature, the reaction mixture was extracted with benzene (100 ml), and the extract was washed with 1 N sodium hydroxide, water, and saturated aqueous sodium chloride After drying over magnesium sulfate, the solvent was evaporated under a reduced pressure and the residue obtained was purified by medium pressure column chromatography using silica gel, to obtain 4-(4-nitrophenoxy)phenol methyl ether (1.5 g).

Workup

  1. extractionthe reaction mixture was extracted with benzene (100 ml)
  2. washthe extract was washed with 1 N sodium hydroxide, water, and saturated aqueous sodium chloride
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customthe residue obtained
  6. customwas purified by medium pressure column chromatography

Sources & evidence

ORD record
ord-3d4be8bb13cb48f28d3fca89e414599a
Source dataset
uspto-grants-1993_04
Patent number
US05205855

Reaction notes

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