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

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Reaction Steps

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).

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