Hydrochloric Acid → 1-Propanone, 1-(7-methoxy-1,3-benzodioxol-5-yl)-

HRID 618129Notes

Reaction equation

HRID 618129 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]2[O:13][CH2:12][O:11][C:10]=12)[CH:6]=[O:7].[CH2:14]([Mg]Br)[CH3:15].Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6](=[O:7])[CH2:14][CH3:15])[CH:8]=[C:9]2[O:13][CH2:12][O:11][C:10]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 220161,3-Benzodioxole-5-carboxaldehyde, 7-methoxy-HCID 178418443HCID 178418443, compound

Product 1

HCID 1770991-Propanone, 1-(7-methoxy-1,3-benzodioxol-5-yl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methoxy-4,5-methylenedioxybenzaldehyde (5.55 g) was dissolved in tetrahydrofuran (150 ml), and ethylmagnesium bromide (IM tetrahydrofuran solution, 46.2 ml) was added thereto, followed by stirring at room temperature for 30 minutes. 1N Hydrochloric acid was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, a 5% aqueous solution of sodium bicarbonate and a saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in acetone (300 ml), and Jones' reagent (5.3 ml) was added thereto under ice-cooling, followed by stirring at the same temperature for 30 minutes. 2-Propanol (5.3 ml) was added to the reaction solution and the mixture was concentrated under reduced pressure. The residue was subjected to partitioning between ethyl acetate and water. The organic layer was washed successively with water and a saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 3'-methoxy-4',5'-methylenedioxypropiophenone (5.27 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water
  3. dry with materiala 5% aqueous solution of sodium bicarbonate and a saturated saline, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in acetone (300 ml)
  6. additionJones' reagent (5.3 ml) was added
  7. temperatureunder ice-cooling
  8. stirringby stirring at the same temperature for 30 minutes
  9. addition2-Propanol (5.3 ml) was added to the reaction solution
  10. concentrationthe mixture was concentrated under reduced pressure
  11. customto partitioning between ethyl acetate and water
  12. washThe organic layer was washed successively with water
  13. dry with materiala saturated saline, dried over anhydrous magnesium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9e76eb6d992248818fa6121f8802fba0
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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