Potassium Iodide → HCID 10469118, compound

HRID 1681920Notes

Reaction equation

HRID 1681920 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([OH:10])=[C:5]([CH3:11])[CH:4]=1)#[N:2].[OH-].[K+].[I-].[K+].Cl[CH:17]([CH3:26])[CH2:18][C:19]1[O:23][N:22]=[C:21]([CH2:24][CH3:25])[CH:20]=1>C(#N)C>[CH3:11][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[C:7]([CH3:9])[C:6]=1[O:10][CH2:26][CH2:17][CH2:18][C:19]1[O:23][N:22]=[C:21]([CH2:24][CH3:25])[CH:20]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 201763,5-Dimethyl-4-hydroxybenzonitrileHCID 19804385HCID 19804385, compound

Product 1

HCID 10469118HCID 10469118, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 7.84 g 4-cyano-2,6-dimethylphenol, 3.57 g potassium hydroxide and 10.6 g potassium iodide in 200 ml acetonitrile was added 12 g 5-(2-chloropropyl)-3-ethylisoxazole, and the mixture was heated at reflux for about 16 hrs. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was washed with aqueous sodium hydroxide (10%) until the excess starting phenol was removed, and the solution concentrated to give 10 g of 5-[3-(2,6-dimethyl-4-cyanophenoxy)propyl]-3-ethylisoxazole as a yellow oil. A sample of the latter was obtained in crystalline form, m.p. 50°-51° C. by crystallization from methanol at -50° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for about 16 hrs
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between ethyl acetate and water
  5. washThe ethyl acetate layer was washed with aqueous sodium hydroxide (10%) until the excess starting phenol
  6. customwas removed
  7. concentrationthe solution concentrated

Sources & evidence

ORD record
ord-4088dc8ed0e04f9690e4dd02d8893512
Source dataset
uspto-grants-1992_12
Patent number
US05175178

Reaction notes

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