Potassium Carbonate → Methyl [(2H-1,3-benzodioxol-5-yl)oxy]acetate

HRID 1738573Notes

Reaction equation

HRID 1738573 reaction equation
[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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68289Sesamol

Product 1

HCID 22998410Methyl [(2H-1,3-benzodioxol-5-yl)oxy]acetateYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b534e537c1784f4aa9996baf71d42d7f
Source dataset
uspto-grants-1999_10
Patent number
US05962490

Reaction notes

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