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

HRID 2372269

Reaktionsgleichung

Reaktionsgleichung von HRID 2372269
[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, of potassium carbonate, 530 mg of 5-bromopentanenitrile and 0.2 g 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 raphy on silica gel eluting with 40% ethyl etate in hexane to provide 200 mg of the desired title product, m.p. =105°-106° C.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3c82aabff1734efcb02168530377f18c
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05098613

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