Hydrochloric Acid → 1,4-Phenylenedioxydiacetic acid

Participants

Reaction Conditions

Reaction Steps

(4-Methoxycarbonylmethoxy-phenoxy)-acetic acid methyl ester 82 (100 grams, 394 mmol) was added to 3.25 M-sodium hydroxide solution (600 mL) and heated to 70° C. for 20 hours and poured onto ice cold water (1 lit) and the pH adjusted to 1 with concentrated hydrochloric acid. Crude 83 was filtered, dried, and recrystallized from DMF by precipitating with water to give pure 83 (60 grams, 67.4%) as a white powder. M.p: 254-256.5° C. IH NMR (CDCl3+DMSO, d6) 4.44 (s, 2H, OCH2), 6.72 (s, 2H, Ar).

Provenance & Evidence