Reaction #2122466

Reaction equation

4,4′-bis(chloromethyl)-1,1′-biphenyl

p-xylene

→

4,4′-bis(2,5-dimethylbenzyl)-1,1′-biphenyl

Solvents

ethanol

Conditions

Workup

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

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.

Source