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

HRID 1690196Notes

Reaction equation

HRID 1690196 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+].[CH2:17](Br)[CH:18]=[CH2:19].C(OCC)(=O)C>CC(C)=O>[CH2:19]([O:10][C:8]1[CH:9]=[C:4]([C:2](=[O:3])[CH3:1])[CH:5]=[CH:6][CH:7]=1)[CH:18]=[CH2:17]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 84873-HydroxyacetophenoneHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 2579581-[3-(allyloxy)phenyl]ethanoneYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Hydroxyacetophenone (1.36 g, 10.0 mmol) was dissolved in acetone (50 mL), then added with potassium carbonate (2.76 g, 20.0 mmol) and allylbromide (1.27 mL, 15.0 mmol) at room temperature, and heated to reflux for 2 hours. The reaction solution was cooled to room temperature, added with ethyl acetate, and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (n-hexane/ethyl acetate=10/1), and 1-(3-(allyloxy)phenyl)ethanone (1.76 g, 100%) was obtained as a pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified

Sources & evidence

ORD record
ord-3f68f85c097b4ec9907422162010a9b5
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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