反应详情

To 79.2 g (1.65 m) of 50% sodium hydride suspended in 750 ml DMSO was added dropwise a mixture of 121.6 g (0.75 mole) p-nitrophenylacetonitrile and 161.7 ml (0.75 mole) 1,4 dibromobutane in 750 ml of a 50:50 mixture of DMSO, diethyl ether. The temperature was held between 25°-30° C. The reaction mixture was stirred at room temperature overnight then cooled to 10° C. Thirty-eight ml of isopropanol was added followed by the cautious addition of 2.8 l of water. Air was bubbled through the black reaction mixture to remove most of the ether. Black solid was filtered and taken up in diethyl ether. The ether solution was washed two times with 2 N HCl and two times with brine, dried over MgSO4, and concentrated in vacuo. The resulting dark solid was extracted six times with boiling hexane. The hexane solution was concentrated to a small volume to yield 127.5 g of product, melting point 76°-77° C.

1. additionwas added dropwise
2. customwas held between 25°-30° C
3. temperaturethen cooled to 10° C
4. customAir was bubbled through the black reaction mixture
5. customto remove most of the ether
6. filtrationBlack solid was filtered
7. washThe ether solution was washed two times with 2 N HCl and two times with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated in vacuo
10. extractionThe resulting dark solid was extracted six times with boiling hexane
11. concentrationThe hexane solution was concentrated to a small volume