Sodium Hydroxide → 2-[(2,6-Dichlorophenyl)amino]-5-(3-phenoxybenzyl)benzene acetic acid

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Reaction Steps

A solution of the ester (2.2 g, 4.3 mmol) of Step A in dioxane (20 mL) containing 1N NaOH (7 mL) is heated at reflux under nitrogen for 4 hrs. The solvent is removed and the residue is partitioned between dilute HCl and ether (30 mL each). The organic phase is washed with brine, dried (Na2SO4) and filtered. The filtrate is treated with tris(hydroxymethyl)aminomethane (0.485 g) in methanol (20 mL). The solvent is evaporated to a syrup in vacuo and diluted with ethyl acetate. The crystalline solid is collected (white solid, 1.6 g, 60%) and recrystallized from methanol-water to provide the pure title compound (0.89 g, m.p. 137°-138° C.).

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