Potassium Iodide → 5-[(3-Phenylprop-2-en-1-yl)oxy]-2H-1,3-benzodioxole

HRID 917980Notes

Reaction equation

HRID 917980 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.[CH2:11](Cl)[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:1]1[O:2][C:3]2[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]=[CH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:6][C:4]=2[O:5]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68289SesamolHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 542755455-[(3-Phenylprop-2-en-1-yl)oxy]-2H-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of sesamol (27.6 g.), cinnamyl chloride (30.4 g.), anhydrous potassium carbonate (50.0 g.), potassium iodide (2.0 g.) in anhydrous acetone (100 ml.) was heated under reflux for 1.5 hrs. The acetone was removed by evaporation, and the residue was treated with excess water and cooled to give an oil, which subsequently solidified. The crude product was collected by filtration and recrystallized from methanol to give MDCB as colorless prisms, m.p. 83° C., yield 15.0 g. (Found: C, 75.4; H, 5.67. Calculated for C16H14O3 : C, 75.6; H, 5.55.) The nuclear magnetic resonance (NMR) spectrum of MDCB at 100 MHz in deuterated chloroform (CDCl3) exhibited absorbances as follows: a doublet (2 protons) at δ 4.59 (coupling constant J = 6.0 Hz), a singlet (2 protons) at δ 5.89 a multiplet (5 protons) at δ 6.22-6.80, and a multiplet (5 protons) at δ 7.18-7.48.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hrs
  3. customThe acetone was removed by evaporation
  4. additionthe residue was treated with excess water
  5. temperaturecooled
  6. customto give an oil, which
  7. filtrationThe crude product was collected by filtration
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-4b0b3cf1c62740a580a68fbeadf125c5
Source dataset
uspto-grants-1976_07
Patent number
US03968234

Reaction notes

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