反应详情

温度

4 °C

To a 500 mL flask, equipped with mechanical stirrer and under inert atmosphere, was added acetanilide (50 g, 370 mmol), succinic anhydride (37 g, 370 mmol), and 200 mL carbon disulfide. The reaction vessel was cooled with an external ice bath while aluminum (III) trichloride (185 g, 1390 mmol) was added over 1 hour. Additional carbon disulfide (75 mL) was added, the reaction stirred for 1 hour with external ice bath, and then stirred at room temperature for 18 hours. The reaction vessel was cooled with an external ice bath and ice (75 mL) was added to the reaction to quench. The mixture was transferred to a 2 L beaker and ice was added until the final volume was 1400 mL. The insoluble material was collected by suction filtration and washed with 2×100 mL of water. The solid was then dissolved in 1000 mL of 8% aqueous sodium bicarbonate and stirred for 3 hours, diluted with an additional 200 mL of water, and filtered to remove insoluble impurities. The filtered solution was acidified with 1 M aqueous hydrochloric acid until pH=2. The crude product precipitate was collected by filtration and was re dissolved in hot (80-85° C.) water (1250 mL), insoluble material removed by decanting and the mixture cooled to 4° C. The product (8.45 g, 10%) was isolated by filtration as yellow off-white crystals. Found: C, 61.20, H, 5.63%, N, 5.94%; C12H23NO4 requires C, 61.27; H, 5.58%, N, 5.96%; 1H NMR (d6-DMSO): δ 12.2, s, 1H (COOH); δ 10.3, s, 1H(NH); δ 7.9, d, 2H (aryl H's); δ 7.7 d, 2H (aryl H's); 3.2, t, 2H(CH2 α to carbonyl); δ 2.6, t, 2H(CH2 α to COOH); δ 2.1, s, 3H(CH3).

1. customTo a 500 mL flask, equipped with mechanical stirrer and under inert atmosphere
2. additionwas added over 1 hour
3. stirringstirred at room temperature for 18 hours
4. temperatureThe reaction vessel was cooled with an external ice bath
5. customto quench
6. additionwas added until the final volume
7. filtrationThe insoluble material was collected by suction filtration
8. washwashed with 2×100 mL of water
9. dissolutionThe solid was then dissolved in 1000 mL of 8% aqueous sodium bicarbonate
10. stirringstirred for 3 hours
11. additiondiluted with an additional 200 mL of water
12. filtrationfiltered
13. customto remove insoluble impurities
14. filtrationThe crude product precipitate was collected by filtration
15. dissolutionwas re dissolved in hot (80-85° C.) water (1250 mL), insoluble material
16. customremoved
17. customby decanting