Hydrochloric Acid → 5-(4'-Hydroxy-3'methoxyphenyl)pentadienoic acid prenylamide

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Reaction Steps

To a solution of 1.34 g of 5-(4'-ethoxycarbonyloxy-3'-methoxyphenyl)pentadienoic acid prenylamide in 10 ml of methanol are added 2.8 ml of 2N aqueous solution of sodium hydroxide followed by stirring at room temperature for 15 min. The mixture is acidified with 1N hydrochloric acid and then extracted with chloroform. The organic layer is washed with water and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure, and the residue is subjected to column chromatography on silica gel. From the fraction eluted with methylene chloride is obtained 0.77 g of 5-(4'-hydroxy-3'methoxyphenyl)pentadienoic acid prenylamide (11). Spectroscopic data of the product support the structure of the formula (11) below.

Provenance & Evidence