1,3-Dimethyl-2-imidazolidinone → 4-(4-Methylphenoxy)-1,1′-biphenyl

HRID 703303Notes

Reaction equation

HRID 703303 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCN(C)C1=O>C1(C)C=CC=CC=1>[C:18]1([CH3:21])[CH:19]=[CH:20][C:15]([O:13][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][CH:11]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinone2×HCID 71034-HydroxybiphenylHCID 78104-Chlorotoluene2×HCID 11430Potassium Carbonate

Product 1

HCID 146702664-(4-Methylphenoxy)-1,1′-biphenylYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A four-necked flask equipped with a thermometer, a stirrer, and a reflux condenser with a water trap was charged with 554.7 g of p-phenylphenol, 607.7 g of p-chlorotoluene, 265.4 g of potassium carbonate, 8.0 g of 8-hydroxyquinoline-copper complex and 82 g of 1,3-dimethyl-2-imidazolidinone. The mixture was stirred at 140° to 180° C. under nitrogen for 5 hours while the temperature was raised gradually. The material which was collected in the trap was removed from time to time. After 15 hours of further heating at 170° to 185°C. with stirring, the ratio of p-phenylphenol and 4-biphenylyl p-tolyl ether in the reaction mixtures was found to be 1.5:98.5 as determined by GLC (gas-liquid chromatography) on the area ratio basis. Thereafter, the resulting mixture was concentrated under reduced pressure (10 mmHg) to give 270 g of a distillate composed of p-chlorotoluene and 1,3-dimethyl-2-imidazolidinone. Toluene (400 ml) was added to the residue for dissolving the reaction product. The organic layer was washed with a 10% sodium hydroxide solution, 10% sulfuric acid, and water, in that order. The toluene was then distilled off under reduced pressure to give 796 g of crude, light brown 4-biphenylyl p-tolyl ether in 95% yield. Distillation of the crude product under reduced pressure (2 mmHg) at 190° to 195° C. to give 775 g (92% yield) of white 4-biphenylyl p-tolyl ether melting at 97° to 99° C.

Workup

  1. customA four-necked flask equipped with a thermometer, a stirrer, and a reflux condenser with a water trap
  2. temperaturewas raised gradually
  3. customThe material which was collected in the trap
  4. customwas removed from time to time
  5. temperatureAfter 15 hours of further heating at 170° to 185°C.
  6. stirringwith stirring
  7. customthe ratio of p-phenylphenol and 4-biphenylyl p-tolyl ether in the reaction mixtures
  8. concentrationThereafter, the resulting mixture was concentrated under reduced pressure (10 mmHg)
  9. customto give 270 g of
  10. dissolutionfor dissolving the reaction product
  11. washThe organic layer was washed with a 10% sodium hydroxide solution, 10% sulfuric acid, and water, in that order
  12. distillationThe toluene was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-8a27b242874c40df88b093ea8065e4f0
Source dataset
uspto-grants-1991_01
Patent number
US04982010

Reaction notes

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