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

HRID 487076

Reaction equation

HRID 487076 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, 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.

Workup

  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

Sources & evidence

ORD record
ord-1886765b8fa645018b6508e81fcfb758
Source dataset
uspto-grants-1994_03
Patent number
US05294613

Linked notes

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