Potassium Iodide → 2'-Allyloxyacetophenone

HRID 557387Notes

Reaction equation

HRID 557387 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH2:11](Br)[CH:12]=[CH2:13].C(=O)([O-])[O-:16].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:11]([O:16][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:3](=[O:4])[CH3:2])[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 2994412'-Allyloxyacetophenone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

542 g (3.9 mol) of 2-hydroxyacetophenone are heated to reflux with 592 g (4.9 mol) of allyl bromide, 1000 g (7.2 mol) of potassium carbonate and 13.2 g (79 mmol) of potassium iodide in 2.4 liters of acetone for 24 h. Cooling to room temperature is followed by filtration and removal of the solvent in vacuo. The residue is dissolved in toluene and washed with 10% strength sodium hydroxide solution and water. Concentration results in 689 g (98% of theory) of the title compound.

Workup

  1. filtrationis followed by filtration and removal of the solvent in vacuo
  2. dissolutionThe residue is dissolved in toluene
  3. washwashed with 10% strength sodium hydroxide solution and water
  4. concentrationConcentration

Sources & evidence

ORD record
ord-51972aa0d0034b78893c5dc5353c35a5
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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