反应详情

A mixture of 3-(3,5-Dimethyl-phenyl)-acrylonitrile (93) (15.7 g, 0.1M), NBS (18.58 g, 0.11M) and benzoyl peroxide (2.42 g, 10 mmol) in carbon tetrachloride (120 ml) was refluxed for 3 hr. under a light of 500 W tungsten lamp. After cooling to room temperature, the mixture was filtered and the filterate was evaporated in vacuo. The residue was dissolved in ether, washed with aqueous saturated sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a crude product as a light yellow solid (94). A mixture of the crude product (94) and potassium cyanide (9.75 g, 0.15M) in ethanol (60 ml) and distilled water (30 ml) was refluxed for 2 hr. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was partitioned between EA-ether (1:1) and water. The organic layer was taken, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:1 to 2:1)) to afford 6.68 g (36%) of a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 2.39 (3H, s), 3.74 (2H, s), 5.91 (1H, d, J=16.5 Hz), 7.21 (3H, s), 7.34 (1H, d, J=16.5 Hz).

1. temperaturewas refluxed for 3 hr
2. filtrationthe mixture was filtered
3. customthe filterate was evaporated in vacuo
4. dissolutionThe residue was dissolved in ether
5. washwashed with aqueous saturated sodium bicarbonate solution
6. dry with materialdried with anhydrous magnesium sulfate
7. filtrationfiltered
8. customevaporated in vacuo
9. customto give a crude product as a light yellow solid (94)
10. distillationdistilled water (30 ml)
11. temperaturewas refluxed for 2 hr
12. temperatureAfter cooling to room temperature
13. customthe mixture was evaporated in vacuo
14. customthe residue was partitioned between EA-ether (1:1) and water
15. dry with materialdried with anhydrous magnesium sulfate
16. filtrationfiltered
17. customevaporated in vacuo
18. customThe residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:1 to 2:1))