Potassium Iodide → 5-(2,4-Diacetyl-5-hydroxyphenoxy)pentanenitrile

HRID 487076

Reaktionsgleichung

Reaktionsgleichung von HRID 487076
[C:1]([C:4]1[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[C:7]([OH:8])=[CH:6][C:5]=1[OH:14])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27].[I-].[K+]>>[C:1]([C:4]1[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[C:7]([OH:8])=[CH:6][C:5]=1[O:14][CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])(=[O:3])[CH3:2]

Komponenten

5

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 750974,6-DiacetylresorcinolHCID 794355-Bromopentanenitrile

Produkt 1

HCID 148200535-(2,4-Diacetyl-5-hydroxyphenoxy)pentanenitrileAusbeute 24,2 %

Versuchsvorschrift

A mixture of 582 mg of 4,6-diacetylresorcinol, 460 mg of potassium carbonate, 530 mg of 5-bromopentanenitrile and 0.2 9 of potassium iodide was heated at reflux overnight. The mixture was concentrated in vacuo and partitioned between ethyl acetate and dilute hydrochloric acid. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel eluting with 40% ethyl acetate in hexane to provide 200 mg of the desired title product, m.p.=105°-106° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. custompartitioned between ethyl acetate and dilute hydrochloric acid
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative thin layer chromatography on silica gel eluting with 40% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-1886765b8fa645018b6508e81fcfb758
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294613

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