Acetone → Methyl 3,5-diallyloxyphenylacetate

HRID 499868

Reaktionsgleichung

Reaktionsgleichung von HRID 499868
[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]

Komponenten

5

Edukt 4

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

Produkt 1

HCID 23116191Methyl 3,5-diallyloxyphenylacetateAusbeute 93 %

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d046dce58fb9440189cdfb0335cbb7e5
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767693B2

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