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

HRID 703304Notes

Reaction equation

HRID 703304 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.CN1CCN(C)C1=O.[OH-].[Na+]>C(O)(C)C>[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-imidazolidinoneHCID 71034-HydroxybiphenylHCID 78104-ChlorotolueneHCID 14798Sodium Hydroxide

Product 1

HCID 146702664-(4-Methylphenoxy)-1,1′-biphenylYield 94%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 340 g of p-phenylphenol, 630 g of p-chlorotoluene, 68 g of 1,3-dimethyl-2-imidazolidinone and 81.0 g of sodium hydroxide was stirred at 160° to 168° C., and the water was separated azeotropically was removed by means of a trap. After adding 5.0 g of 8-hydroxyquinoline-copper complex, the mixture was further stirred at 155° to 165° C. for 15 hours. GLC analysis showed that the conversion of p-phenylphenol to the desired product was 98%. The same after treatment as in Example 1 gave 490 g of a crude product in 94% yield. It was dissolved in isopropyl alcohol, decolorized with active carbon and clay, and recrystallized to give 4-biphenylyl p-tolyl ether as white crystals melting at 97° to 98° C.

Workup

  1. customthe water was separated azeotropically
  2. customwas removed by means of a trap
  3. additionAfter adding 5.0 g of 8-hydroxyquinoline-copper complex
  4. stirringthe mixture was further stirred at 155° to 165° C. for 15 hours
  5. customThe same after treatment as in Example 1 gave 490 g of a crude product in 94% yield
  6. customrecrystallized

Sources & evidence

ORD record
ord-43f2fe3cf7634149b0177f78f38db780
Source dataset
uspto-grants-1991_01
Patent number
US04982010

Reaction notes

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