Hydrochloric Acid → 4-[[2-(Methoxy)ethyl]oxy]-alphaoxobenzeneacetic acid

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A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid (0.498 g) in dimethylsulfoxide (5 mL) under argon was treated with 4N sodium hydroxide (1.5 mL), stirred for 5 minutes and treated with the mesylate prepared from 2-methoxyethanol (0.462 g) . The mixture was heated at 60° C. for 3 hours and poured into excess 1N hydrochloric acid. The product was extracted into diethyl ether (3×50 mL) and the organic layers were washed in turn with water (2×25 mL). The combined organic layers were dried (Na2SO4), filtered, and evaporated to give 0.56 g of crude product as a solid. Crystallization from ethyl acetate-hexane provided 0.3 g of 4-[[2-(methoxy)ethyl]oxy]-alphaoxobenzeneacetic acid, mp 129°-130° C.

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