反応 #2122467

反応方程式

4,4′-bis(chloromethyl)-1,1′-biphenyl

toluene

→

4,4′-bis(4-methylbenzyl)-1,1′-biphenyl

溶媒

ethanol

反応条件

後処理

1. 1
   workup.ADDITIONa second 1 mL aliquot of catalyst was added
2. 2
   workup.STIRRINGAfter stirring overnight at room temperature
3. 3
   濃縮The organic layer was concentrated to dryness under vacuum on a rotary evaporator
4. 4
   workup.ADDITIONtreated with MgSO4
5. 5
   ろ過Vacuum filtration through glass fiber
6. 6
   ろ過filter paper
7. 7
   その他gave a clear solution to which 200 mL heptane
8. 8
   workup.ADDITIONwas added while hot
9. 9
   温度The slightly turbid solution was cooled to room temperature
10. 10
    workup.WAITin a freezer overnight to complete
11. 11
    その他crystallization
12. 12
    その他White crystals, 17.4 g, mp=161.8 C, were recovered

実験手順

A 500 mL flask was charged with 4,4′-bis(chloromethyl)-1,1′-biphenyl (25.1 g) and toluene (300 mL). To the clear solution stirring at room temperature was added titanium tetrachloride (1 mL) and the mixture instantly became dark brown. After 5 minutes, a second 1 mL aliquot of catalyst was added. After stirring overnight at room temperature, ethanol (10 mL) was added to kill the catalyst, and the mixture became a light, cream colored suspension. The organic layer was concentrated to dryness under vacuum on a rotary evaporator. The tan solid was suspended in 200 mL boiling toluene and treated with MgSO4. Vacuum filtration through glass fiber filter paper gave a clear solution to which 200 mL heptane was added while hot. The slightly turbid solution was cooled to room temperature, then in a freezer overnight to complete crystallization. White crystals, 17.4 g, mp=161.8 C, were recovered. GC/MS, HNMR, CNMR and IR were all consistent with the desired product.

出典