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

Participants

Reaction Steps

A solution of the ester (2.75 g, 0.0106 mole) in 95% ethanol (20 ml) was treated with 50% sodium hydroxide (10 ml) and water (10 ml), and refluxed for one hour. The ethanol was removed in vacuo and replaced with water, and the aqueous solution was extracted with ether (20 ml) and adjusted to pH~4 with concentrated hydrochloric acid (16 ml). A solid soon precipitated, and this was filtered, washed with water, air dried, and recrystallized from ethyl acetate (2 crops) to afford 2.03 g (78%) of the title compound as fine pale tan needles; mp 119°-120° C.

Provenance & Evidence