Iodine → 2-[3,4-(Methylenedioxy)phenyl]-2-butanol

HRID 2259774Notes

Reaction equation

HRID 2259774 reaction equation
II.[Mg].Br[CH2:5][CH3:6].[C:7]([C:10]1[CH:18]=[CH:17][C:13]2[O:14][CH2:15][O:16][C:12]=2[CH:11]=1)(=[O:9])[CH3:8].[Cl-].[NH4+]>O1CCCC1.O>[O:14]1[C:13]2[CH:17]=[CH:18][C:10]([C:7]([OH:9])([CH2:5][CH3:6])[CH3:8])=[CH:11][C:12]=2[O:16][CH2:15]1

Participants

8

Reactant 5

HCID 807IodineHCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 76622AcetopiperoneHCID 5462224Magnesium

Product 1

HCID 190016982-[3,4-(Methylenedioxy)phenyl]-2-butanolYield 95.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

15 ml of tetrahydrofuran and a catalytic amount of iodine were added to 340 mg of magnesium ribbon to obtain a mixture. 1.59 g of bromoethane was gradually added to the mixture in a stream of nitrogen in such a way that the reaction system was mildly refluxed. The resulting mixture was heated under reflux for 30 minutes and cooled, followed by the addition of a solution of 2 g of 5 -acetyl-1,3-benzodioxole in tetrahydrofuran. The obtained mixture was stirred at a room temperature for 20 minutes, followed by the addition of a saturated aqueous solution of ammonium chloride and water. The obtained mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of common salt, dried over ahydrous magnesium sulfate and filtered. The filtrate was distilled to remove the solvent. 2.27 g of the title compound was obtained as a crude oil.

Workup

  1. customto obtain a mixture
  2. temperaturewas mildly refluxed
  3. temperatureThe resulting mixture was heated
  4. temperatureunder reflux for 30 minutes
  5. temperaturecooled
  6. extractionThe obtained mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous solution of common salt
  8. dry with materialdried over ahydrous magnesium sulfate
  9. filtrationfiltered
  10. distillationThe filtrate was distilled
  11. customto remove the solvent

Sources & evidence

ORD record
ord-1668fad0a7184ee29c1e47d2edd15a0c
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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