Allyl bromide → 2'-Allyloxyacetophenone

HRID 1819561Notes

Reaction equation

HRID 1819561 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11](=[O:14])([O-])[O-].[K+].[K+].[CH2:17](Br)[CH:18]=C>CC(C)=O.C(OCC)C>[CH2:11]([O:14][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:3](=[O:4])[CH3:2])[CH:17]=[CH2:18]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 2994412'-AllyloxyacetophenoneYield 51%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirring suspension of 2-hydroxyacetophenone 72 (5 ml, 42 mmol) and potassium carbonate (6.516 g, 47 mmol, 1.1 equ) in acetone (30 ml) was added allyl bromide (4 ml, 46 mmol, 1.1 equ). The reaction was heated to reflux for 20 hours. The reaction was then concentrated in vacuo, taken up in water and extracted into ethyl acetate (2×). The organic layer was then dried (MgSO4) and concentrated in vacuo to give an yellow oil. This was taken up in diethyl ether, washed with 1M potassium hydroxide then dried (MgSO4) and concentrated in vacuo to give 1-(2-allyloxy-phenyl)-ethanone (3.70 g, 51%) as a pale yellow oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 20 hours
  3. concentrationThe reaction was then concentrated in vacuo
  4. extractionextracted into ethyl acetate (2×)
  5. dry with materialThe organic layer was then dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give an yellow oil
  8. washwashed with 1M potassium hydroxide
  9. dry with materialthen dried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5104c59827c74c269a7e792afd2fbe8a
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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