P-Xylene → 4,4'-Bis(2,5-dimethylbenzyl)-1,1'-biphenyl

HRID 2035284

Reaktionsgleichung

Reaktionsgleichung von HRID 2035284
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15]Cl)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1>[Ti](Cl)(Cl)(Cl)Cl.C(O)C>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:4]3[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=3[CH3:2])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 7809P-XyleneHCID 742754,4'-Bis(chloromethyl)-1,1'-biphenyl

Produkt 1

HCID 585267414,4'-Bis(2,5-dimethylbenzyl)-1,1'-biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A 100mL flask was charged with 4,4′-bis(chloromethyl)-1,1′-biphenyl (1.0 g) and p-xylene (25 mL). To the clear solution stirring at room temperature was added titanium tetrachloride (6 drops) and the mixture instantly became dark brown. After stirring overnight at room temperature, ethanol (2mL) was added to kill the catalyst, and the mixture became a light, cream colored suspension. The mixture was transferred to a separatory funnel and washed with dilute aqueous HCl followed by saturated aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate, and concentrated to dryness under vacuum on a rotary evaporator. The tan solid was recrystallized from toluene yielding a white crystalline product, mp=144.6 C. GC/MS, HNMR, CNMR and IR were all consistent with the desired product.

Aufarbeitung

  1. stirringAfter stirring overnight at room temperature
  2. customThe mixture was transferred to a separatory funnel
  3. washwashed with dilute aqueous HCl
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated to dryness under vacuum on a rotary evaporator
  6. customThe tan solid was recrystallized from toluene yielding a white crystalline product, mp=144.6 C

Quellen und Nachweise

ORD-Eintrag
ord-b6cc3255943c4ee2ab27ee67d0f892cc
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08574323B2

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