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

HRID 2035284

Reaction equation

HRID 2035284 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b6cc3255943c4ee2ab27ee67d0f892cc
Source dataset
uspto-grants-2013_11
Patent number
US08574323B2

Linked notes

Loading…