반응 #2175452

반응 방정식

HCl

AlCl3

4-Fluorenecarboxylic acid

HCl

succinic anhydride

→

7-(3-carboxy-propionyl)-4-fluorenecarboxylic acid

용매

1,2-dichloroethane

반응 조건

후처리

1. 1
   기타was placed in a room temperature
2. 2
   기타The reaction was very carefully quenched by the slow portion-wise addition of 3 M HCl (Caution
3. 3
   기타The reaction
4. 4
   workup.ADDITIONis added too rapidly
5. 5
   workup.ADDITION) The final well mixed suspension
6. 6
   기타The organic solvent was removed at reduced pressure
7. 7
   여과the product was filtered
8. 8
   세척washed well with water
9. 9
   workup.DISSOLUTIONThe crude product was dissolved in warm NaOH solution (approximately ≦1 M NaOH),
10. 10
    여과filtered
11. 11
    기타precipitated with the addition of concentrated HCl
12. 12
    여과The product was filtered
13. 13
    세척washed with water
14. 14
    건조dried at reduced pressure in the presence of P2O5

실험 절차

In a dry argon-purged round bottom flask anhydrous AlCl3 (26.9 g, 0.202 mol) was suspended in anhydrous 1,2-dichloroethane (60 mL). 4-Fluorenecarboxylic acid (10.0, g, 0.048 mol) was added to the suspension. The reaction flask was placed in a room temperature bath and succinic anhydride (5.72 g, 0.057 mol) was carefully added. The reaction was stirred for five hours and then cooled to 0° C. The reaction was very carefully quenched by the slow portion-wise addition of 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 and the product was filtered and washed well with water. The crude product was dissolved in warm NaOH solution (approximately ≦1 M 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 (14.3 g, 97%). 1H-NMR (d6-DMSO): δ (ppm) 8.4 (d, 1H, Ar); 8.2 (s, 1H, Ar); 8.0 (d, 1H, Ar); 7.8 (m, 2H, Ar); 7.5 (t, 1H, Ar); 4.1 (s, 2H, CH2); 2.6 (t, 2H, CH2) 2.5 (under DMSO, CH2).

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