反应详情

温度

45 °C

Add acetic acid (45 mL), concentrated sulfuric acid (5.4 grams, 0.055 moles), water (10 mL), 9-fluoreneone (9.01 grams, 0.05 moles), iodine (6.0 grams, 0.0237 moles), and periodic acid (2.85 grams, 0.0125 moles) to a 250 mL, 3-neck round-bottom flask equipped with a magnetic stirrer, internal temperature probe, heating mantle, and a glycol-cooled condenser fitted with a nitrogen inlet. Heat the reaction mixture to 45° C. and stir 1 hour, then warm to 50° C. and stir an additional 2.5 hrs. Warm the mixture to 60° C. and add additional acetic acid (45 mL). Stir the reaction mixture for an additional 10 hours, cool to room temperature and stir the reaction mixture at room temperature for about 8 hours. Collect the precipitate by filtration. Transfer the filter cake and acetic acid (40 mL) to a 250 mL, 3-neck round-bottom flask equipped with a magnetic stirrer, internal temperature probe, heating mantle, and a glycol-cooled condenser fitted with a nitrogen inlet. Heat the mixture to 70° C. and add additional acetic acid with continued warming until a clear solution is observed. Reduce the reaction mixture to 50° C. and stir at 50° C. for 2 hours. Slowly cool the reaction mixture to 25° C. and stir 1 hour. Recover the precipitate by vacuum filtration. Air-dried the resulting filter cake to provide the title compound (10.2 g, 66.6% yield). 1H NMR (CDCl3, 500.0 MHz): δ 7.95 (d, 1H, J=1.5); 7.81 (dd, 1H, J=2, 8); 7.64 (d, 1H, J=7.5); 7.50 (m, 2H); 7.33-7.24 (m, 2H).

1. customequipped with a magnetic stirrer
2. temperatureinternal temperature probe, heating mantle
3. customfitted with a nitrogen inlet
4. temperaturewarm to 50° C.
5. stirringstir an additional 2.5 hrs
6. temperatureWarm the mixture to 60° C.
7. stirringStir the reaction mixture for an additional 10 hours
8. temperaturecool to room temperature
9. stirringstir the reaction mixture at room temperature for about 8 hours
10. customCollect the precipitate
11. filtrationby filtration
12. customequipped with a magnetic stirrer
13. temperatureinternal temperature probe, heating mantle
14. temperaturea glycol-cooled condenser
15. customfitted with a nitrogen inlet
16. temperatureHeat the mixture to 70° C.
17. additionadd additional acetic acid
18. temperaturewith continued warming until a clear solution
19. customto 50° C.
20. stirringstir at 50° C. for 2 hours
21. temperatureSlowly cool the reaction mixture to 25° C.
22. stirringstir 1 hour
23. customRecover the precipitate
24. filtrationby vacuum filtration
25. customAir-dried the resulting
26. filtrationfilter cake