Potassium Carbonate → Methyl (1,3-benzodioxol-5-yloxy)acetate

HRID 1166998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166998
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:3]=2[O:2]1.Br[CH2:12][C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]1[O:2][C:3]2[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:6][C:4]=2[O:5]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68289Sesamol

Produkt 1

HCID 22998410Methyl (1,3-benzodioxol-5-yloxy)acetateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

The mixture of sesamol (13.8 g, 100 mmol, methyl bromoacetate (15.3 g, 100 mmol) and potassium carbonate in acetone (200 ml) was refluxed for 24 h with stirring. Acetone was removed under reduced pressure. The residue was dissolved in water (200 ml) and was extracted with ether (2×100 ml). the combined organic layer was dried over magnesium sulfate and the solvent removed under reduced pressure to give methyl 2-[3,4-(methylenedioxy)phenoxy]acetate as an oil (12 g, 57% yield). The aqueous phase was neutralized to pH 2-3 with concentrated HCl and the precipitated solid was filtered to get 2-[3,4-(methylenedioxy)phenoxy]acetic acid as a solid (6 g, 31% yield).

Aufarbeitung

  1. temperaturewas refluxed for 24 h
  2. customAcetone was removed under reduced pressure
  3. dissolutionThe residue was dissolved in water (200 ml)
  4. extractionwas extracted with ether (2×100 ml)
  5. dry with materialthe combined organic layer was dried over magnesium sulfate
  6. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0e2cf49696c5428c90e45280635f7ba7
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613804B2

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