反应 #6169

反应方程式

1-(5-chloropentoxy)-2-methoxybenzene

potassium carbonate

4-Cyanophenol

potassium iodide

→

4-[5-(2-methoxyphenoxy)pentoxy]benzonitrile

溶剂

dimethyl sulfoxide

反应条件

后处理

1. 1
   workup.ADDITIONis added
2. 2
   温度This suspension is heated at 80°-82° C. for 7 hours
3. 3
   其他the heating bath is then removed
4. 4
   workup.ADDITIONthe mixture is poured onto cold water (29 L)
5. 5
   其他the product precipitates
6. 6
   萃取This mixture is then extracted with ethyl acetate (3×20 L)
7. 7
   洗涤The organic extracts are washed with potassium hydroxide solution (0.50N, 4×8 L), brine (2×10 L)
8. 8
   干燥dried over anhydrous sodium sulfate
9. 9
   过滤filtered
10. 10
    浓缩concentrated in vacuo
11. 11
    其他to yield a yellow oil which
12. 12
    其他crystallizes
13. 13
    workup.DISSOLUTIONThis is then dissolved in 2-propanol (5.6 L)
14. 14
    温度with warming
15. 15
    过滤the resulting solution is filtered gravimetrically
16. 16
    洗涤washing the funnel with 1.2 L of hot 2-propanol
17. 17
    温度The combined filtrate is cooled to 10° C. in an ice bath
18. 18
    过滤filtered
19. 19
    洗涤The filter cake is washed with 2-propanol (2×800 mL)
20. 20
    其他dried in vacuo

实验过程

4-Cyanophenol (742 g, 6.23 mol) is dissolved in dimethyl sulfoxide (7.30 L) and to this solution is added powdered anhydrous potassium carbonate (883 g, 6.30 mol), potassium iodide (1.05 kg, 6.30 mol) and finally 1-(5-chloropentoxy)-2-methoxybenzene (1.44 kg, 6.29 mol). This suspension is heated at 80°-82° C. for 7 hours and the heating bath is then removed. After stirring overnight at room temperature, the mixture is poured onto cold water (29 L) and the product precipitates. This mixture is then extracted with ethyl acetate (3×20 L). The organic extracts are washed with potassium hydroxide solution (0.50N, 4×8 L), brine (2×10 L), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield a yellow oil which crystallizes on standing. This is then dissolved in 2-propanol (5.6 L) with warming and the resulting solution is filtered gravimetrically, washing the funnel with 1.2 L of hot 2-propanol. The combined filtrate is cooled to 10° C. in an ice bath and the solid mass is broken up and filtered. The filter cake is washed with 2-propanol (2×800 mL), dried in vacuo to give 4-[5-(2-methoxyphenoxy)pentoxy]benzonitrile, m.p. 66°-68° C. which is >99.5% pure by glc analysis.

来源