Reaktion #158253

Reaktionsgleichung

propylene oxide

4,4′dimethoxy-o-terphenyl

iodine

toluene

→

material

Ausbeute 72.0%

2,11-dimethoxytriphenylene

Ausbeute 72.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe photoreactor was set up with a condenser
2. 2
   Temperaturcooled by a circulating chiller
3. 3
   Temperaturwas maintained at between 20° C. and 25° C. (
4. 4
   FiltrationA solid was filtered off
5. 5
   Waschenwashed with hexanes, only recovered 2.2 g of material
6. 6
   workup.ADDITIONThe filtrate was diluted with toluene
7. 7
   Waschenwashed with sodium sulfate solution
8. 8
   ExtraktionThe aqueous layer was back extracted with toluene
9. 9
   Trocknenthe organic layers were dried over magnesium sulfate
10. 10
    Filtrationfiltered
11. 11
    Sonstigeevaporated
12. 12
    workup.DISSOLUTIONMaterial was dissolved in toluene
13. 13
    workup.ADDITIONadded sodium sulfite solution
14. 14
    SonstigeThe layers were separated
15. 15
    Extraktionthe aqueous layer extracted with toluene
16. 16
    Trocknenthe combined organic layers were dried over magnesium sulfate
17. 17
    Filtrationfiltered
18. 18
    Sonstigeevaporated
19. 19
    SonstigeThe residue was purified by column chromatography
20. 20
    Wascheneluting with 0 to 100% ethyl acetate/hexane

Vorschrift

12.4 g (42.7 mmol) of 4,4′dimethoxy-o-terphenyl and 16 g (63.0 mmol) iodine chips was placed in a 250 mL reaction vessel. 200 mL of toluene was added followed by 30 mL of propylene oxide. The photoreactor was set up with a condenser cooled by a circulating chiller. A 400 W medium pressure mercury lamp was used as the light source. The reaction vessel was placed in a cabinet. The lamp was ignited and the chiller temperature was set such that the water exiting the reactor was maintained at between 20° C. and 25° C. (monitored by a thermocouple attached the exit stream). The reaction was left on for 18 hours. A solid was filtered off and washed with hexanes, only recovered 2.2 g of material. The filtrate was diluted with toluene and washed with sodium sulfate solution. The aqueous layer was back extracted with toluene and the organic layers were dried over magnesium sulfate, filtered, and evaporated. Material was dissolved in toluene and added sodium sulfite solution and stirred. The layers were separated, the aqueous layer extracted with toluene and the combined organic layers were dried over magnesium sulfate, filtered, and evaporated. The residue was purified by column chromatography eluting with 0 to 100% ethyl acetate/hexane. 8.8 g material (72%) was obtained.

Quelle