反応 #1929005

反応方程式

8-chloro-1-octanol

pyridine

SOCl2

→

Polymer 9

収率 95.0%

Chlorooctane

収率 95.0%

溶媒

THF

反応条件

後処理

1. 1
   その他The Schlenk was connected to a trap with a NaOH solution (2M) for absorption of HCl and SO2
2. 2
   温度The temperature was slowly increased
3. 3
   workup.DISTILLATIONExcess of SOCl2 and THF were distilled off under vacuum at 50° C. for 30 minutes
4. 4
   workup.ADDITIONThen freshly distilled THF (30 ml) was added
5. 5
   workup.DISSOLUTIONto dissolve the acylated polymer
6. 6
   workup.DISSOLUTIONAfter 30 minutes needed for complete dissolution of polymer
7. 7
   その他The polymer was recovered
8. 8
   その他by precipitating
9. 9
   workup.DISTILLATIONinto distilled water
10. 10
    その他The product purification
11. 11
    workup.DISSOLUTIONwas made by dissolution in hot CH2Cl2
12. 12
    その他precipitation in ethanol
13. 13
    その他drying at 50° C. in vacuum oven

実験手順

1 g (0.0015 mol, equivalent weight=666 gram per mole repeat unit) polymer 5 was placed into a 50 ml Schlenk and dissolved in THF anhydrous (30 ml). The Schlenk was connected to a trap with a NaOH solution (2M) for absorption of HCl and SO2. Then pyridine anhydrous 0.5 ml (0.0062 mol), and SOCl2 0.3 ml (0.0041 mol) were added dropwise at room temperature into the Schlenk. The temperature was slowly increased and maintained at 60° C. for 3 h. Excess of SOCl2 and THF were distilled off under vacuum at 50° C. for 30 minutes, the resulting crude acid chloride polymer. Then freshly distilled THF (30 ml) was added to dissolve the acylated polymer. After 30 minutes needed for complete dissolution of polymer, a solution of excess 8-chloro-1-octanol 1.05 ml (2 mol.eq, 0.0062 mol) was added dropwise to the polymer solution at room temperature under vigorous stirring, and allowed to stir for 24 h. The polymer was recovered by precipitating into distilled water. The product purification was made by dissolution in hot CH2Cl2, precipitation in ethanol and drying at 50° C. in vacuum oven to obtain Polymer 9 as a brown solid (1.39 g, yield 95%) with the following characteristics:

出典