Potassium Iodide → 6-(4-Acetyl-3-hydroxy-2-propylphenoxy)hexane nitrile

HRID 543218Notes

Reaction equation

HRID 543218 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].Cl[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C>[C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:14][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])=[C:4]([CH2:3][CH2:2][CH3:1])[C:9]=1[OH:10])(=[O:12])[CH3:13]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2465226-chlorohexanenitrileHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 137633146-(4-Acetyl-3-hydroxy-2-propylphenoxy)hexane nitrile

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 44.4 g. of 2,4-dihydroxy-3-propylacetophenone, 42.2 g. of 6-chlorocapronitrile, 33.2 g. of potassium carbonate and 4.0 g. of potassium iodide in one liter of methyl ethyl ketone was allowed to reflux for three days. The reaction mixture was filtered and the filtrate was evaporated in vacuo. Chromatography of the residue over silica gel (0-30% ethyl acetate gradient in hexane) gave 53.6 g. of the title product as an oil.

Workup

  1. temperatureto reflux for three days
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customChromatography of the residue over silica gel (0-30% ethyl acetate gradient in hexane) gave 53.6 g

Sources & evidence

ORD record
ord-f18112f1e0c146a59299340790a54379
Source dataset
uspto-grants-1987_04
Patent number
US04661505

Reaction notes

Loading…