Water → 4-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester

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Reaction Steps

A suspension of 60% sodium hydride/oil dispersion (1.0 g, 25 mmoles) in anhydrous dimethylformamide (40 ml) under nitrogen was treated with methyl 4-amino-5-chloro-2-hydroxybenzoate (4.03 g, 20 mmoles), stirred for 30 minutes, then treated with 2-bromoethyl methyl ether (3.48 g, 25 mmoles). The mixture was heated to 95°±5° C. for 1.5 hours, then cooled and added to water (250 ml). The aqueous suspension was filtered, and the solid was washed with water, air dried, and recrystallized from ether/hexane to yield 2.75 g (53%) of product, 121°-122.5° C.

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