18-Crown-6 → HCID 54559320, compound

HRID 1728300Notes

Reaction equation

HRID 1728300 reaction equation
[K].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.C1OCCOCCOCCOCCOCCOC1.I[CH2:39][CH2:40][CH2:41][OH:42]>C(#N)C>[OH:42][CH2:41][CH2:40][CH2:39][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 693903-Iodo-1-propanolHCID 139676Phenol, 4-[2-(4-nitrophenyl)ethenyl]-HCID 5462222Potassium

Product 1

HCID 54559320HCID 54559320, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The potassium salt of 4-hydroxy-4'-nitrostilbene from Example 4 (280 g, 1 m), acetonitrile (2 liters) and the catalyst 18-Crown-6 (1 g) were charged into a 4 liter 3 necked flask equipped with a reflux condenser, mechanical stirrer, a heating mantle, and an addition funnel, and provided with argon atmosphere. The mixture was kept gently refluxing and stirring, while 3-iodopropan-1-ol (223 g, 1.2 m) was added dropwise over a period of about 3 hours. The reaction mixture was refluxed for about 24 hours. About a liter of the solvent was then distilled off at atmospheric pressure, and the reaction mixture was allowed to cool to ambient temperature. The yellow solid was filtered, dried, and recrystallized from toluene to yield yellow crystals of compound of Formula 28. Yield 210 g (70%).

Workup

  1. customequipped with a reflux condenser, mechanical stirrer
  2. customa heating mantle, and an addition funnel, and provided with argon atmosphere
  3. temperatureThe mixture was kept gently refluxing
  4. additionwas added dropwise over a period of about 3 hours
  5. temperatureThe reaction mixture was refluxed for about 24 hours
  6. distillationAbout a liter of the solvent was then distilled off at atmospheric pressure
  7. filtrationThe yellow solid was filtered
  8. customdried
  9. customrecrystallized from toluene

Sources & evidence

ORD record
ord-0bb6e782b7884a4bb7c8f4df25cff3ba
Source dataset
uspto-grants-1994_07
Patent number
US05326661

Reaction notes

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