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

HRID 1600854Notes

Reaction equation

HRID 1600854 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-d599dd21a614425199a629e1b89a6d40
Source dataset
uspto-grants-1999_11
Patent number
US05977117

Reaction notes

Loading…