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

HRID 703303ノート

反応式

HRID 703303 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 146702664-(4-Methylphenoxy)-1,1'-biphenyl収率 95%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8a27b242874c40df88b093ea8065e4f0
出典データセット
uspto-grants-1991_01
特許番号
US04982010

反応ノート

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