Sodium Iodide → HCID 13923412, compound

HRID 1253105Notes

Reaction equation

HRID 1253105 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[C:12]2[O:14][CH2:15][O:16][C:11]2=[C:10]([O:17][CH3:18])[CH:9]=1)(=O)=O.[I-:19].[Na+]>CC(C)=O>[CH3:18][O:17][C:10]1[CH:9]=[C:8]([CH2:7][CH2:6][I:19])[CH:13]=[C:12]2[O:14][CH2:15][O:16][C:11]=12

Participants

4

Reactant 2

HCID 5238Sodium Iodide2×HCID 13923409HCID 13923409, compound

Product 1

HCID 13923412HCID 13923412, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.45 g (19.9 mmol) of 2-(3-methoxy-4,5-methylenedioxyphenyl)ethyl methanesulfonate (4) and 3.58 g (23.9 mmol) of sodium iodide were added to 100 ml of acetone and refluxed under heating for 2 hours. To this reaction mixture was added again 0.89 g (5.9 mmol) of sodium iodide, and the reaction mixture was refluxed under heating for 3 hours and 20 minutes. After the refluxed mixture was cooled, the deposited salt was filtered out and washed with acetone. The filtrate and the acetone used for washing were combined and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluate: ethyl acetate n-hexane=1/2) to obtain 5.80 g of 2-(3-methoxy-4,5-methylenedioxyphenyl) ethyl iodide (7) as a crystal with a yield of 95%, which was recrystallized from n-hexane/ethyl acetate. Melting point: 78°-80° C.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 2 hours
  3. temperaturethe reaction mixture was refluxed
  4. temperatureunder heating for 3 hours and 20 minutes
  5. temperatureAfter the refluxed mixture was cooled
  6. filtrationthe deposited salt was filtered out
  7. washwashed with acetone
  8. washfor washing
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (eluate: ethyl acetate n-hexane=1/2)

Sources & evidence

ORD record
ord-6e75dc1589f14d43b68535412b4b5f70
Source dataset
uspto-grants-1988_05
Patent number
US04746747

Reaction notes

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