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

HRID 1110662Notes

Reaction equation

HRID 1110662 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 1N 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 1N 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-3b259a2574ea40a788f6b3d4830be565
Source dataset
uspto-grants-1990_12
Patent number
US04976773

Reaction notes

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