Potassium Iodide → 4-Allyloxybenzophenone

HRID 358381Notes

Reaction equation

HRID 358381 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].[CH2:18](Cl)[CH:19]=[CH2:20].[I-].[K+]>O1CCCC1>[CH2:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1)[CH:19]=[CH2:18]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7850Allyl chlorideHCID 143474-HydroxybenzophenoneHCID 14797Potassium Hydroxide

Product 1

HCID 2579104-Allyloxybenzophenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxybenzophenone (100 parts) was dissolved in tetrahydrofuran (100 parts). Potassium hydroxide (30.9 parts) was added, heated and stirred until completely dissolved. Allyl chloride (46.4 parts) and potassium iodide (42 parts) were added to this solution. The mixture was refluxed for 8 hours. After cooling, it was washed with water and the solvent removed by distillation. A crude product of the desired 4-allyloxybenzophenone was obtained. It was recrystallized in n-hexane to obtain 110 parts of 4-allyloxybenzophenone (melting point 71° C.) at 72% yield.

Workup

  1. temperatureheated
  2. dissolutionuntil completely dissolved
  3. temperatureThe mixture was refluxed for 8 hours
  4. temperatureAfter cooling
  5. washit was washed with water
  6. customthe solvent removed by distillation

Sources & evidence

ORD record
ord-033a6afd5d024ad08e38130c84c05ddf
Source dataset
uspto-grants-1984_08
Patent number
US04467082

Reaction notes

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