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

HRID 2372269

Reaction equation

HRID 2372269 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

HCID 148200535-(2,4-Diacetyl-5-hydroxyphenoxy)pentanenitrileYield 24.2%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3c82aabff1734efcb02168530377f18c
Source dataset
uspto-grants-1992_03
Patent number
US05098613

Linked notes

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