Allyl bromide → 5-[(Prop-2-en-1-yl)oxy]-2H-1,3-benzodioxole

HRID 1386438Notes

Reaction equation

HRID 1386438 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[CH2:5]1[O:9][C:8]2[CH:10]=[C:11]([OH:14])[CH:12]=[CH:13][C:7]=2[O:6]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][CH2:3][CH:2]=[CH2:1])=[CH:10][C:8]=2[O:9]1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 68289Sesamol

Product 1

HCID 5862725-[(Prop-2-en-1-yl)oxy]-2H-1,3-benzodioxoleYield 96.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Allyl bromide (1.75 g., 14 mmol) was added to a solution of sesamol (2.0 g, 14 mmol) that had been dissolved in 50 ml of dry acetone, followed by addition of powdered potassium carbonate (2.4 g, 17 mmol) and the resulting cloudy solution was refluxed for 18 h. The solution was cooled and the solvent removed in vacuo. The remaining suspension was extracted into ether and the organic layer was washed with water (1×25 ml ), brine solution (1×25 ml ), and dried over MgSO4. Concentration of solvent yielded 2.4 g (94%) of a pale yellow oil which was used in the next step with no further purification.

Workup

  1. temperaturethe resulting cloudy solution was refluxed for 18 h
  2. temperatureThe solution was cooled
  3. customthe solvent removed in vacuo
  4. extractionThe remaining suspension was extracted into ether
  5. washthe organic layer was washed with water (1×25 ml ), brine solution (1×25 ml )
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-41ad98a26cd640b89dfbb55229aab7da
Source dataset
uspto-grants-2001_07
Patent number
US06265428B1

Reaction notes

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