반응 #6169

반응 방정식

1-(5-chloropentoxy)-2-methoxybenzene

potassium carbonate

4-Cyanophenol

potassium iodide

→

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

용매

dimethyl sulfoxide

반응 조건

후처리

1. 1
   workup.ADDITIONis added
2. 2
   온도This suspension is heated at 80°-82° C. for 7 hours
3. 3
   기타the heating bath is then removed
4. 4
   workup.ADDITIONthe mixture is poured onto cold water (29 L)
5. 5
   기타the product precipitates
6. 6
   추출This mixture is then extracted with ethyl acetate (3×20 L)
7. 7
   세척The organic extracts are washed with potassium hydroxide solution (0.50N, 4×8 L), brine (2×10 L)
8. 8
   건조dried over anhydrous sodium sulfate
9. 9
   여과filtered
10. 10
    농축concentrated in vacuo
11. 11
    기타to yield a yellow oil which
12. 12
    기타crystallizes
13. 13
    workup.DISSOLUTIONThis is then dissolved in 2-propanol (5.6 L)
14. 14
    온도with warming
15. 15
    여과the resulting solution is filtered gravimetrically
16. 16
    세척washing the funnel with 1.2 L of hot 2-propanol
17. 17
    온도The combined filtrate is cooled to 10° C. in an ice bath
18. 18
    여과filtered
19. 19
    세척The filter cake is washed with 2-propanol (2×800 mL)
20. 20
    기타dried in vacuo

실험 절차

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.

출처