Реакция #2175459

Уравнение реакции

AlCl3

fluorene

HCl

AlCl3

succinic anhydride

HCl

→

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

Растворители

1,2-dichloroethane

1,2-dichloroethane

Условия реакции

Обработка

1. 1
   ДругоеIn a dry agon-purged round bottom flask
2. 2
   Другоеwas placed in a room temperature
3. 3
   Другоеvery carefully quenched by slow addition to cold 3 M HCl (Caution
4. 4
   ДругоеThe reaction
5. 5
   workup.ADDITIONis added too rapidly
6. 6
   workup.ADDITION) The final well mixed suspension
7. 7
   ДругоеThe organic solvent was removed at reduced pressure
8. 8
   Фильтрацияthe product was filtered
9. 9
   Промывкаwashed well with water
10. 10
    workup.DISSOLUTIONThe crude product was dissolved in warm NaOH solution (approximately <1M NaOH),
11. 11
    Фильтрацияfiltered
12. 12
    Другоеprecipitated with the addition of concentrated HCl
13. 13
    ФильтрацияThe product was filtered
14. 14
    Промывкаwashed with water
15. 15
    Сушкаdried at reduced pressure in the presence of P2O5

Методика

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).

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