Potassium Iodide → 2'-Allyloxyacetophenone

HRID 1669745Notes

Reaction equation

HRID 1669745 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 litres 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-75c005e32b1542e88d72c44a964ac89c
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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