Allyl bromide → 1-[3-(allyloxy)phenyl]ethanone

HRID 1244122Notes

Reaction equation

HRID 1244122 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH:19]=[CH2:20]>CC(C)=O>[CH2:20]([O:10][C:8]1[CH:9]=[C:4]([C:2](=[O:3])[CH3:1])[CH:5]=[CH:6][CH:7]=1)[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 84873-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 2579581-[3-(allyloxy)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To solution of 3-hydroxyacetophenone (2.140 g, 15.72 mmol) in acetone (100 mL) was added potassium carbonate (4.344 g, 31.43 mmol), and 3-bromo-propene (2.282 g, 18.86 mmol) and the reaction was stirred at room temperature for 16 h. The solvent was removed in vacuo and water (25 mL) was added to the reaction mixture and then extracted with ethyl acetate (3×60 mL). The organic extracts were washed with brine (15 mL), dried (Na2SO4) and concentrated to give the title compound which was used as is in the next step.

Workup

  1. customThe solvent was removed in vacuo and water (25 mL)
  2. additionwas added to the reaction mixture
  3. extractionextracted with ethyl acetate (3×60 mL)
  4. washThe organic extracts were washed with brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8d3c60a8585e4faca3a916616cb0bc63
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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