Hydrochloric Acid → (+/-)-5-(2-Formyl-3-hydroxyphenoxy)-2-methylpentanoic acid

참여 물질

반응 단계

To a stirred solution of (±)-ethyl 5-(2-formyl-3-methoxyphenoxy)-2-methylpentanoate (5.3 g, 0.018 M) in dry tetrahydrofuran (50 ml) was added dropwise a solution of magnesium iodide (7.44 g, 0.027 M) in dry ether (100 ml). The mixture was then stirred under reflux (51/2 hr). The cooled mixture, containing (±)-ethyl 5-(2-formyl-3-hydroxyphenoxy)-2-methylpentanoate, was poured into 10% hydrochloric acid (50 ml), the organic layer was separated and the aqueous phase extracted with ethyl acetate. The combined organic solutions were washed with water and extracted with 2 N sodium hydroxide solution. The combined extracts were acidified with concentrated hydrochloric acid with cooling and the solid produced filtered off and washed with water to give (±)-5-(2-formyl-3-hydroxyphenoxy)-2-methylpentanoic acid, m.p. 70°-70.5° C. from benzene/petrol.

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