反应详情

A 500 mL round bottom flask equipped with a magnetic stirrer bar and an inert atmosphere (nitrogen gas) was charged with 5.25 mL (48.3 mmol) of anisole, 4.83 g (48.3 mmol) of succinic anhydride, 125 mL 1,1,2,2-tetrachloroethane and 125 mL of nitrobenzene. The reaction vessel was cooled with an external ice bath and stirred for 30 minutes. Aluminum trichloride (14.2 g, 106.4 mmol) was added to the pale yellow solution, which then turned to a dark reddish brown color. The ice bath was removed, and the reaction was allowed to stir at room temperature for 36 hours. Reaction was again cooled with an external ice bath. Prepared acidic solution by pouring 1N hydrogen chloride solution into a 100 mL beaker filled with ice. This solution was added to the reaction mixture carefully, drop-wise at first until reaction became clear with white precipitate. After that point a 10 mL portion was carefully added to test for reactivity, and then the remained of the ice/acid mixture was added. A second 100 mL of ice/acid mixture was added, the external ice bath removed and the pale emulsion was stirred for 2 hours. A white precipitate was collected form the emulsion by suction filtration. This solid was dissolved in 300 mL of 0.3 M sodium hydroxide, washed with 100 mL of ethyl acetate, and acidified to ˜pH 1 with 1 M hydrochloric acid. The white precipitate that was collected upon vacuum filtration was washed with 3×100 mL de-ionized water and dried. The product (4.7 g, 47%) was isolated as a white solid, mp 149-150° C. Combustion analysis: Found: C, 63.52; H, 5.78%; C11H12O4 requires C, 63.45; H, 5.81% 1H NMR (d6-DMSO): δ 12.2, s, 1H (COOH); δ 7.9 d, 2H (aryl H's); δ 7.0, d, 2H, (arylH's); δ 3.8, s, 3H (OMe H's); δ 3.2, t, 2H(CH2 α to carbonyl); δ 2.5, t, 2H(CH2 α to COOH).

1. customA 500 mL round bottom flask equipped with a magnetic stirrer bar
2. temperatureThe reaction vessel was cooled with an external ice bath
3. customThe ice bath was removed
4. stirringto stir at room temperature for 36 hours
5. customReaction
6. temperaturewas again cooled with an external ice bath
7. additionbeaker filled with ice
8. additionThis solution was added to the reaction mixture carefully
9. customfirst until reaction
10. additionAfter that point a 10 mL portion was carefully added to test for reactivity
11. additionwas added
12. customthe external ice bath removed
13. stirringthe pale emulsion was stirred for 2 hours
14. customA white precipitate was collected form the emulsion
15. filtrationby suction filtration
16. dissolutionThis solid was dissolved in 300 mL of 0.3 M sodium hydroxide
17. washwashed with 100 mL of ethyl acetate
18. filtrationThe white precipitate that was collected upon vacuum filtration
19. washwas washed with 3×100 mL de-ionized water
20. customdried