Potassium Iodide → HCID 54082516, compound

HRID 918002Notes

Reaction equation

HRID 918002 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:10][CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][O:16][CH:17]([CH3:19])[CH3:18].[CH2:21]1[O:29][C:28]2[CH:27]=[CH:26][C:25]([OH:30])=[CH:24][C:23]=2[O:22]1>CC(C)=O>[CH:17]([O:16][CH2:15][CH2:14][C:13]([CH3:20])=[CH:12][CH2:11][CH2:10][O:30][C:25]1[CH:26]=[CH:27][C:28]2[O:29][CH2:21][O:22][C:23]=2[CH:24]=1)([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68289SesamolHCID 54298637HCID 54298637, compound

Product 1

HCID 54082516HCID 54082516, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.35 g (0.017 mol) of potassium carbonate and 50 mg of potassium iodide are added to a solution of 4.0 g (0.017 mol) of 1-bromo-6-isopropoxy-4-methyl-3-hexene and 2.35 g (0.017 mol) of 3,4-methylendioxy-phenol in 120 cc of acetone. The suspension is boiled under reflux during the course of 20 hours, is then filtered and liberated from acetone in a vacuum. The residue is taken up in ether, washed with water and saturated salt solution, dried over sodium sulphate and evaporated. The residue is chromatographed on silica gel with hexane/ethyl acetate 9:1. Thus the cis/trans isomeric mixture of the 5-(6-isopropoxy-4-methyl methyl-3-hexenyloxy)-1,3-benzodioxol is obtained as colourless oil. nD20 = 1.5111.

Workup

  1. temperatureunder reflux during the course of 20 hours
  2. filtrationis then filtered
  3. washwashed with water and saturated salt solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue is chromatographed on silica gel with hexane/ethyl acetate 9:1
  7. additionThus the cis/trans isomeric mixture of the 5-(6-isopropoxy-4-methyl methyl-3-hexenyloxy)-1,3-benzodioxol
  8. customis obtained as colourless oil

Sources & evidence

ORD record
ord-e1abc156563249ed8c72239fc4d2a43f
Source dataset
uspto-grants-1976_07
Patent number
US03968235

Reaction notes

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