Sodium Hydroxide → 4-[3-[3-Hydroxy-4-(methoxycarbonyl)-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid

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Reaction Steps

As in Example 19, a solution of 4-[3-[3-hydroxy-4-(methoxycarbonyl)-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.3 g) in methanol (30 mL) was treated with 4N sodium hydroxide (0.53 mL) and then was stirred at room temperature for 1 hour. Most of the solvents were removed in vacuo, then the mixture was acidified with 3N hydrochloric acid and extracted with ethyl acetate. The dried (MgSO4) extracts were evaporated and the crude acid was crystallized from a carbon tetrachloride-hexane mixture containing a small amount of dichloromethane to yield 0.164 g of 4-[3-[3-hydroxy-4-(methoxycarbonyl)-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid, as a colorless solid, mp 86°-87° C.

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