Reaktion #1929005

Reaktionsgleichung

8-chloro-1-octanol

pyridine

SOCl2

→

Polymer 9

Ausbeute 95.0%

Chlorooctane

Ausbeute 95.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe Schlenk was connected to a trap with a NaOH solution (2M) for absorption of HCl and SO2
2. 2
   TemperaturThe 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
   SonstigeThe polymer was recovered
8. 8
   Sonstigeby precipitating
9. 9
   workup.DISTILLATIONinto distilled water
10. 10
    SonstigeThe product purification
11. 11
    workup.DISSOLUTIONwas made by dissolution in hot CH2Cl2
12. 12
    Sonstigeprecipitation in ethanol
13. 13
    Sonstigedrying at 50° C. in vacuum oven

Vorschrift

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:

Quelle