Reaktion #2175459

Reaktionsgleichung

AlCl3

fluorene

HCl

AlCl3

succinic anhydride

HCl

→

2,7-di(3-carboxy-propionyl)fluorene

Lösungsmittel

1,2-dichloroethane

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a dry agon-purged round bottom flask
2. 2
   Sonstigewas placed in a room temperature
3. 3
   Sonstigevery carefully quenched by slow addition to cold 3 M HCl (Caution
4. 4
   SonstigeThe reaction
5. 5
   workup.ADDITIONis added too rapidly
6. 6
   workup.ADDITION) The final well mixed suspension
7. 7
   SonstigeThe organic solvent was removed at reduced pressure
8. 8
   Filtrationthe product was filtered
9. 9
   Waschenwashed well with water
10. 10
    workup.DISSOLUTIONThe crude product was dissolved in warm NaOH solution (approximately <1M NaOH),
11. 11
    Filtrationfiltered
12. 12
    Sonstigeprecipitated with the addition of concentrated HCl
13. 13
    FiltrationThe product was filtered
14. 14
    Waschenwashed with water
15. 15
    Trocknendried at reduced pressure in the presence of P2O5

Vorschrift

In a dry agon-purged round bottom flask, anhydrous AlCl3 (98 g, 0.735 mol) was suspended in anhydrous 1,2-dichloroethane (140 mL). In a separate flask, fluorene (23 g, 0.138 mol) was dissolved in anh. 1,2-dichloroethane (125 mL) then added to the AlCl3 suspension. The reaction flask was placed in a room temperature bath and succinic anhydride (34.5 g, 0.345 mol) was carefully added. The reaction was stirred for 16 hours and then very carefully quenched by slow addition to cold 3 M HCl (Caution! The reaction can react violently when HCl is added too rapidly.) The final well mixed suspension was acidic and not reactive to additional HCl solution. The organic solvent was removed at reduced pressure then the product was filtered and washed well with water. The crude product was dissolved in warm NaOH solution (approximately <1M NaOH), filtered and precipitated with the addition of concentrated HCl. The product was filtered, washed with water and then dried at reduced pressure in the presence of P2O5. The product was a pale yellow solid (49.3 g, 97%). 1H-NMR (CD3OD): δ (ppm) 8.3 (s, 2H, Ar); 8.2 (m, 2H, Ar); 8.1 (m, 2H, Ar); 4.1 (s, 2H, CH2); 3.5 (t, 4H, CH2); 2.8 (t, 4H, CH2).

Quelle