反应详情

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.

1. additiona second 1 mL aliquot of catalyst was added
2. stirringAfter stirring overnight at room temperature
3. concentrationThe organic layer was concentrated to dryness under vacuum on a rotary evaporator
4. additiontreated with MgSO4
5. filtrationVacuum filtration through glass fiber
6. filtrationfilter paper
7. customgave a clear solution to which 200 mL heptane
8. additionwas added while hot
9. temperatureThe slightly turbid solution was cooled to room temperature
10. waitin a freezer overnight to complete
11. customcrystallization
12. customWhite crystals, 17.4 g, mp=161.8 C, were recovered