Hydrochloric Acid → 3,5-Dimethoxy-4-nitrophenylacetic acid

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Reaction Steps

A stirred solution of t-butyl 3,5-difluoro-4-nitrophenylacetate (4.5 g, Reference Example 14) in methanol (350 mL) was treated with sodium methoxide in methanol (36 g, 25 wt %) and then heated at reflux for 18 hours. The cooled reaction mixture was carefully acidified to pH 2 by addition of dilute hydrochloric acid and then partially evaporated to remove the methanol. The aqueous residue was extracted twice with ethyl acetate. The combined extracts were extracted into saturated sodium bicarbonate solution. The aqueous extract was acidified to pH 2 and extracted with twice with ethyl acetate, then dried and then evaporated to give the title compound (1.4 g) as a brown solid.

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