Hydrochloric Acid → 7-(2-Formyl-3-hydroxyphenoxy)heptanoic acid

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Reaction Steps

To a stirred solution of ethyl 7-(2-formyl-3-methoxyphenoxy)heptanoate (4.15 g, 0.0135 M) in dry tetrahydrofuran (60 ml) was added dropwise a solution of magnesium iodide (5.82 g, 0.0202 M) in dry ether (97.5 ml). The mixture was then stirred under reflux (5 hr). The cooled mixture was poured into 10% hydrochloric acid (65 ml). The organic layer was separated and the aqueous phase extracted with ethyl acetate. The combined organic solution were washed with water and evaporated to dryness. The residue, ethyl 7-(2-formyl-3-hydroxyphenoxyheptanoate, was dissolved in 2 N sodium hydroxide solution (50 ml) with stirring at room temperature (10 hr). The solution was decanted from a residue and acidified with concentrated hydrochloric acid with cooling. The precipitated solid was filtered off and washed well with water to give 7-(2-formyl-3-hydroxyphenoxy)heptanoic acid, m.p. 106°-107° C. from benzene/petrol.

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