Potassium Iodide → 4-[5-(2-Methoxyphenoxy)pentoxy]benzonitrile

HRID 6073

반응식

HRID 6073 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32]>CS(C)=O>[CH3:32][O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 197949041-(5-Chloropentoxy)-2-methoxybenzene

생성물 1

HCID 197948854-[5-(2-Methoxyphenoxy)pentoxy]benzonitrile

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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.

후처리

  1. additionis added
  2. temperatureThis suspension is heated at 80°-82° C. for 7 hours
  3. customthe heating bath is then removed
  4. additionthe mixture is poured onto cold water (29 L)
  5. customthe product precipitates
  6. extractionThis mixture is then extracted with ethyl acetate (3×20 L)
  7. washThe organic extracts are washed with potassium hydroxide solution (0.50N, 4×8 L), brine (2×10 L)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto yield a yellow oil which
  12. customcrystallizes
  13. dissolutionThis is then dissolved in 2-propanol (5.6 L)
  14. temperaturewith warming
  15. filtrationthe resulting solution is filtered gravimetrically
  16. washwashing the funnel with 1.2 L of hot 2-propanol
  17. temperatureThe combined filtrate is cooled to 10° C. in an ice bath
  18. filtrationfiltered
  19. washThe filter cake is washed with 2-propanol (2×800 mL)
  20. customdried in vacuo

출처 및 근거

ORD 기록
ord-9bddb73241f64221b25cad0cce98deec
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246965

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