Reaction #2175452

Reaction equation

HCl

AlCl3

4-Fluorenecarboxylic acid

HCl

succinic anhydride

→

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

Solvents

1,2-dichloroethane

Conditions

Workup

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

Procedure

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).

Source