[4-(4-Benzoylphenyl)phenyl](phenyl)methanone → 4,4'-Bis(1-phenylethenyl)-1,1'-biphenyl

HRID 2050369

Reaktionsgleichung

Reaktionsgleichung von HRID 2050369
C([Li])CCC.C(C1C=CC(C2C=CC(C(=O)C3C=CC=CC=3)=CC=2)=CC=1)(=O)C1C=CC=CC=1.[C:34]1([C:40]([C:42]2[CH:47]=[CH:46][C:45]([C:48]3[CH:53]=[CH:52][C:51]([C:54]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)=[CH2:55])=[CH:50][CH:49]=3)=[CH:44][CH:43]=2)=[CH2:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CCCCCC.[CH:68]([Li:72])([CH2:70][CH3:71])[CH3:69]>C1C=CC=CC=1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:56]1([C:54]([C:51]2[CH:52]=[CH:53][C:48]([C:45]3[CH:44]=[CH:43][C:42]([C:40]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH2:41])=[CH:47][CH:46]=3)=[CH:49][CH:50]=2)=[CH2:55])[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1.[CH:68]([Li:72])([CH2:70][CH3:71])[CH3:69]

Komponenten

9

Edukt 4

HCID 4671929[4-(4-Benzoylphenyl)phenyl](phenyl)methanoneHCID 190788484,4'-Bis(1-phenylethenyl)-1,1'-biphenylHCID 178418339ButyllithiumHCID 178444656HCID 178444656, Verbindung

Produkt 2

HCID 190788484,4'-Bis(1-phenylethenyl)-1,1'-biphenylHCID 178418400CID 53628100

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 241BenzeneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

10.6 millimoles of n-butyllithium as a 0.53 Normal solution in benzene was admixed with 4.06 grams of methyltriphenylphosphonium bromide dissolved in 50 milliliters of tetrahydrofuran in a nitrogen-purged glass reaction vessel and the vessel maintained at ambient temperature (about 22° C.) for a period of 2 hours. A suspension of 2.05 grams of Compound VI in 30 milliliters of tetrahydrofuran was added to the reaction mixture. The reaction vessel was maintained at room temperature for a period of about 16 hours. At the end of this period, the tetrahydrofuran was evaporated and the remaining solid dissolved in a 1:1 by volume diethyl ether-water mixture. The ether and water were separated and the ether layer washed with water and subsequently the ether was evaporated. The crude product Compound VII was recrystallized twice from a 1 to 1 mixture of benzene and ethanol and the solid product obtained washed with n-hexane, the 4,4'-bis(1-phenylethenyl)-1,1'-biphenyl (Compound VII) has a melting point of 193°-196° C. A benzene solution of Compound VII was prepared in a nitrogen-filled serum bottle equipped with a magnetic stirrer. The solution contained 0.5 grams (1.41 millimoles) of Compound VII and 70 milliliters of dry benzene. 7.2 milliliters of 0.482 Normal secondary butyllithium n-hexane solution was injected into the serum bottle with a hypodermic syringe to provide 3.47 milliequivalents of sec-butyllithium. The mixture was stirred at room temperature for 2 hours and 40 minutes, and resulted in a deep blue colored dispersion.

Aufarbeitung

  1. custompurged
  2. customglass reaction vessel
  3. additionwas added to the reaction mixture
  4. temperatureThe reaction vessel was maintained at room temperature for a period of about 16 hours
  5. customAt the end of this period, the tetrahydrofuran was evaporated
  6. dissolutionthe remaining solid dissolved in a 1:1 by volume diethyl ether-water mixture
  7. customThe ether and water were separated
  8. washthe ether layer washed with water
  9. customsubsequently the ether was evaporated
  10. customThe crude product Compound VII was recrystallized twice from a 1 to 1 mixture of benzene and ethanol
  11. customthe solid product obtained
  12. washwashed with n-hexane
  13. additionfilled serum bottle
  14. customequipped with a magnetic stirrer

Quellen und Nachweise

ORD-Eintrag
ord-666e7dc0e9d244bf968ae9f284643e87
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04200718

Verknüpfte Notizen

Wird geladen…