反应详情

To a solution of propylbenzene (14.6 g, 121.4 mmol) in 243 mL of a solution of aluminum chloride in nitrobenzene (1.0M, 243 mmol) was added succinic anhydride (12.15 g, 121.4 mmol). After 3 h, the reaction was quenched with 2N hydrochloric acid, diluted with ether and washed 5 times with dilute hydrochloric acid. The organics were then extracted three times with dilute sodium hydroxide and the combined aqueous layers washed three times with ether. The aqueous layer was then acidified with concentrated hydrochloric acid and extracted twice with ether. The combined ether layers were dried over magnesium sulfate, filtered and concentrated in vacuo to give a brown free flowing solid. This product was disolved in 250 mL of acetic acid and ~1 g of Pearlman's catalyst was added. The mixture was stirred vigorously under 1 atmosphere of hydrogen for 16 h, filtered through a pad of celite and concentrated in vacuo. The product was diluted with toluene and concentrated in vacuo to remove the remaining acetic acid to afford 19.3 g of the title compound as a pale-tan crystalline solid: 400 MHz 1H NMR (CDCl3) δ 7.08 (s, 4H), 2.7-2.3 (m, 6H), 1.94 (m, 2H), 1.62 (m, 2H), 0.93 (t, 3H).

1. customthe reaction was quenched with 2N hydrochloric acid
2. additiondiluted with ether
3. washwashed 5 times with dilute hydrochloric acid
4. extractionThe organics were then extracted three times with dilute sodium hydroxide
5. washthe combined aqueous layers washed three times with ether
6. extractionextracted twice with ether
7. dry with materialThe combined ether layers were dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a brown
11. filtrationfiltered through a pad of celite
12. concentrationconcentrated in vacuo
13. additionThe product was diluted with toluene
14. concentrationconcentrated in vacuo
15. customto remove the remaining acetic acid