Potassium Iodide → 2'-Allyloxyacetophenone

HRID 2170940Notes

Reaction equation

HRID 2170940 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 the solvent is removed 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
  2. customthe solvent is removed in vacuo
  3. dissolutionThe residue is dissolved in toluene
  4. washwashed with 10% strength sodium hydroxide solution and water
  5. concentrationConcentration

Sources & evidence

ORD record
ord-18fd616bb6654714a05ef30ccb4d6d7d
Source dataset
uspto-grants-2015_06
Patent number
US09051316B2

Reaction notes

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