Potassium Hydroxide → a-Methoxymethyl-3,5-dimethoxy-4-(beta-methoxyethoxy)methoxycinnamic acid

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Reaction Steps

A solution of 2.6 g (22.0 mmol) of methyl 3-methoxy-propionate in 5 ml of tetrahydrofuran was added to a solution of 666 mg of sodium hydride in 15 ml of tetrahydrofuran solution with ice cooling, subsequently to the resulting solution was added a solution of 3 g (1.1 mmol) of 3,5-dimethoxy-4-(β-methoxyethoxy)methoxybenzaldehyde in 10 ml of tetrahydrofuran. The mixture was stirred at room temperature for 17 hours. The mixture was extracted with 60 ml of ethyl acetate after adding ice to the solution. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The oily product thus obtained was dissolved in 20 ml of tetrahydrofuran. An aqueous potassium hydroxide solution (740 mg/5 ml) was added to the solution. The mixture was stirred at room temperature for 21 hours. The solution was evaporated under reduced pressure. A 40 ml of water was added to the residue, and the aqueous solution was washed with 30 ml of ethyl acetate. The aqueous layer was neutralized with acetic acid and extracted with 60 ml of methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to give 2.5 g (yield 63.2%) of a desired α-methoxymethyl-3,5-dimethoxy-4-(β-methoxyethoxy)-methoxycinnamic acid.

Provenance & Evidence