Hydrochloric Acid → 2-(2-Acetamido-3-phenoxyphenyl)acetic acid

Participants

Reaction Steps

A mixture of ethyl 2-(2-acetamido-3-phenoxyphenyl)acetate (3.65 g.), potassium hydroxide (1.3 g.) and methanol (50 ml.) was stirred for 4 hours at ambient temperature and then for an hour at 40° C. Methanol was distilled off from the reaction mixture under reduced pressure and the residue was dissolved in water. The solution was washed with diethyl ether, adjusted to pH 1.0 with 5% sulfuric acid and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then evaporated. The residue was recrystallized from a mixture of ethanol and n-hexane to give white needles of the captioned compound (3.1 g.). mp 155° to 156° C. Thus obtained product was dissolved in an aqueous solution of sodium bicarbonate and the solution was adjusted to pH 1.0 with 10% hydrochloric acid. The precipitates were collected by filtration and dried to give the pure compound (2.5 g.), mp 155° to 156° C.

Provenance & Evidence