4-Bromoanisole → 1,1'-Biphenyl, 4,4'-dimethoxy-

HRID 2397604Notes

Reaction equation

HRID 2397604 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH:10]([O-:12])=O.[Na+].[OH-].[Na+]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[Pd].O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:2]2[CH:7]=[CH:6][C:5]([O:12][CH3:10])=[CH:4][CH:3]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 77304-BromoanisoleHCID 14798Sodium HydroxideHCID 2723810Sodium Formate2×

Product 1

HCID 164841,1'-Biphenyl, 4,4'-dimethoxy-

Reagents, catalysts & solvents 3

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

18.7 parts of 4-bromoanisole, 6.8 parts of sodium formate, 64 parts of sodium hydroxide liquor (32%), 60 parts of water, 4 parts of cetyl trimethyl ammonium bromide and 3% palladium-on-charcoal (62% paste, 2 parts) are stirred and heated under reflux for 4 hours. A further 6.8 parts of sodium formate are added, and stirring and heating is continued for a further 18 hours. Steam is then passed through the reaction mixture to remove anisole, and the mixture is cooled and filtered. The filter cake is washed with water, dried at 60°, and extracted with 200 parts of chloroform. The palladium catalyst is recovered by filtration of the chloroform extract, and the chloroform is then distilled under vacuum. The white solid residue is triturated with 500 parts of cold water, collected by filtration, and dried at 60°. 5.2 parts of 4,4'-dimethoxybiphenyl, m.p. 172°-173° are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. temperatureheating
  4. customto remove anisole
  5. temperaturethe mixture is cooled
  6. filtrationfiltered
  7. washThe filter cake is washed with water
  8. customdried at 60°
  9. extractionextracted with 200 parts of chloroform
  10. filtrationThe palladium catalyst is recovered by filtration of the chloroform
  11. extractionextract
  12. distillationthe chloroform is then distilled under vacuum
  13. customThe white solid residue is triturated with 500 parts of cold water
  14. filtrationcollected by filtration
  15. customdried at 60°

Sources & evidence

ORD record
ord-30ec644add91409e9d5715f4d2bdf2a1
Source dataset
uspto-grants-1977_05
Patent number
US04022795

Reaction notes

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