Реакция #6169

Уравнение реакции

1-(5-chloropentoxy)-2-methoxybenzene

potassium carbonate

4-Cyanophenol

potassium iodide

→

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

Растворители

dimethyl sulfoxide

Условия реакции

Обработка

1. 1
   workup.ADDITIONis added
2. 2
   ТемператураThis suspension is heated at 80°-82° C. for 7 hours
3. 3
   Другоеthe heating bath is then removed
4. 4
   workup.ADDITIONthe mixture is poured onto cold water (29 L)
5. 5
   Другоеthe product precipitates
6. 6
   ЭкстракцияThis mixture is then extracted with ethyl acetate (3×20 L)
7. 7
   ПромывкаThe organic extracts are washed with potassium hydroxide solution (0.50N, 4×8 L), brine (2×10 L)
8. 8
   Сушкаdried over anhydrous sodium sulfate
9. 9
   Фильтрацияfiltered
10. 10
    Концентрированиеconcentrated in vacuo
11. 11
    Другоеto yield a yellow oil which
12. 12
    Другоеcrystallizes
13. 13
    workup.DISSOLUTIONThis is then dissolved in 2-propanol (5.6 L)
14. 14
    Температураwith warming
15. 15
    Фильтрацияthe resulting solution is filtered gravimetrically
16. 16
    Промывкаwashing the funnel with 1.2 L of hot 2-propanol
17. 17
    ТемператураThe combined filtrate is cooled to 10° C. in an ice bath
18. 18
    Фильтрацияfiltered
19. 19
    ПромывкаThe filter cake is washed with 2-propanol (2×800 mL)
20. 20
    Другоеdried in vacuo

Методика

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.

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