反应详情

温度

0 °C

To a mixture of benzonitrile (10 g, 96.97 mmol), concentrated sulfuric acid (10 g) and glacial acetic acid (40 mL) was added, with stirring at 0° C., the diacetate (32, 10 g, 19.43 mmol). The solution was stored for 10 h at room temperature, then poured onto ice (150 mL) and extracted with ether (3×100 mL). The ether extracts were washed neutral with water (3×100 mL), and saturated sodium bicarbonate solution, dried (Na2SO4) and evaporated in vacuo. The crude product (21 g) was chromatographed on silica gel eluting with petroleum ether:ether (9:1). The unchanged benzonitrile was first removed. Elution with ether then afforded 11 g (88%) of product which was crystallized from petroleum ether to give analytical sample (33) m.p. 90-92° C. (lit.1 94-95° C.).

1. additionwas added
2. additionpoured onto ice (150 mL)
3. extractionextracted with ether (3×100 mL)
4. washThe ether extracts were washed neutral with water (3×100 mL), and saturated sodium bicarbonate solution
5. dry with materialdried (Na2SO4)
6. customevaporated in vacuo
7. customThe crude product (21 g) was chromatographed on silica gel eluting with petroleum ether:ether (9:1)
8. customThe unchanged benzonitrile was first removed
9. washElution with ether