Reaktion #346534

Reaktionsgleichung

magnesium

phosphorus pentoxide

magnesium

acridone

p-bromostyrene

→

9-(p-vinylphenyl)acridine

Ausbeute 42.1%

Lösungsmittel

benzene

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a four-neck flask equipped with a stirrer, a nitrogen gas inlet tube, a reflux condenser with a calcium chloride tube and a dropping funnel
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   Temperaturunder gentle reflux in a dry nitrogen gas stream
4. 4
   workup.ADDITIONwas added dropwise over a period of two hours
5. 5
   TemperaturAfter refluxing for further 5 hours
6. 6
   Temperaturto cool
7. 7
   workup.ADDITIONpoured onto hydrochloric acid-ice
8. 8
   Sonstigehydrolysis
9. 9
   ExtraktionThe organic layer was extracted with ether
10. 10
    Trocknenthe extract was dried over anhydrous sodium sulfate
11. 11
    workup.DISTILLATIONThe solvent was then distilled off
12. 12
    Sonstigeto obtain a yellow semi-solid
13. 13
    workup.STIRRINGThe mixture was stirred at room temperature for 5 hours
14. 14
    SonstigeThe supernatant liquid separated by decantation
15. 15
    Waschenwas washed with water
16. 16
    Sonstigedried
17. 17
    Einengenconcentrated to dryness
18. 18
    SonstigeThe residue was purified by silica gel chromatography

Vorschrift

Into a four-neck flask equipped with a stirrer, a nitrogen gas inlet tube, a reflux condenser with a calcium chloride tube and a dropping funnel were charged 4.9 g of magnesium cut powder and 50 ml of tetrahydrofuran. 36.6 Grams of p-bromostyrene diluted with tetrahydrofuran to about 4 times the weight was added dropwise under gentle reflux in a dry nitrogen gas stream. After the magnesium had disappeared, a solution consisting of 37.0 g of acridone and 600 ml of tetrahydrofuran was added dropwise over a period of two hours with stirring. After refluxing for further 5 hours, the reaction mixture was allowed to cool and then poured onto hydrochloric acid-ice to effect hydrolysis. The organic layer was extracted with ether and the extract was dried over anhydrous sodium sulfate. The solvent was then distilled off to obtain a yellow semi-solid. Almost the same weight (60 g) of phosphorus pentoxide was added to 500 ml of a solution of the semi-solid in benzene. The mixture was stirred at room temperature for 5 hours and then allowed to stand overnight. The supernatant liquid separated by decantation was washed with water, dried, and then concentrated to dryness. The residue was purified by silica gel chromatography to obtain 22.5 g of 9-(p-vinylphenyl)acridine. Yield 42.1%.

Quelle