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

HRID 274912Notes

Reaction equation

HRID 274912 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[OH-].[K+].Br[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1>[Cu]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

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

Product 1

HCID 80637p-(p-Nitrophenoxy)anisoleYield 49%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
70 °C

Procedure

4-Methoxyphenol (25 g, 0.20 mol) was heated under a nitrogen atmosphere to 70° C. during which time the solid melted. Eighty-five percent potassium hydroxide (12.4 g, 0.19 mol) was added all at once and the mixture stirred at 70° C. for 1 hour. 1-Bromo-4-nitrobenzene (33 g, 0.16 mol) and copper powder (0.1 g, 1.57 mmol) were added and the mixture stirred at 190° C. for 3 hours. After cooling to room temperature, the residue was partitioned between benzene and water. The organic layer was then extracted two times with 5% KOH, dried (MgSO4) and the solvent removed under reduced pressure to give a brown solid. Purification by HPLC (hexane-methylene chloride) gave 4-methoxy-4'-nitrodiphenyl ether as a yellow crystalline solid (19.05 g, 49%), mp 107°-109° C.

Workup

  1. stirringthe mixture stirred at 190° C. for 3 hours
  2. temperatureAfter cooling to room temperature
  3. customthe residue was partitioned between benzene and water
  4. extractionThe organic layer was then extracted two times with 5% KOH
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customto give a brown solid
  8. customPurification by HPLC (hexane-methylene chloride)

Sources & evidence

ORD record
ord-61f799f1b4454094bd904292252fbc75
Source dataset
uspto-grants-1995_02
Patent number
US05391571

Reaction notes

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