Acetone → Methyl 3,5-diallyloxyphenylacetate

HRID 499868

Reaction equation

HRID 499868 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22].[CH3:24][C:25]([CH3:27])=O>>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6]([O:8][CH2:27][CH:25]=[CH2:24])[CH:7]=1)[CH:21]=[CH2:22]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 579787Methyl 3,5-dihydroxyphenylacetate

Product 1

HCID 23116191Methyl 3,5-diallyloxyphenylacetateYield 93%

Procedure

Methyl 3,5-dihydroxyphenylacetate (30 g, 0.17 mol) was dissolved in acetone (0.50 L), and potassium carbonate (91 g, 0.66 mol) and allyl bromide (0.11 L, 1.3 mol) were added thereto at room temperature. The mixture was stirred for 8 hours under heating and reflux, and then stirred at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure, and water was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/15-1/3) to obtain methyl 3,5-diallyloxyphenylacetate (40 g, 93%).

Workup

  1. customat room temperature
  2. temperatureunder heating
  3. temperaturereflux
  4. stirringstirred at room temperature for 10 hours
  5. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  6. additionwas added to the resulting residue
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/15-1/3)

Sources & evidence

ORD record
ord-d046dce58fb9440189cdfb0335cbb7e5
Source dataset
uspto-grants-2010_08
Patent number
US07767693B2

Linked notes

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