Thioglycolic Acid → Beta-Propiolactone

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Reaction Steps

The acids from which the esters are derived are also generally available commercially but may be made if so desired by procedures of long-standing in the chemical arts. Mercaptoacetic acid, for example, may be made by the reaction of sodium hydro-sulfide with sodium chloroacetate and subsequent acidification. β-mercaptopropionic acid is obtained in about 80% yield from the reaction of sodium hydrosulfide with β-propiolactone in acetonitrile and subsequent acidification. Mercaptosuccinic acid may be made by adding hydrogen sulfide across the double bond of maleic anhydride followed by hydrolysis. Also suitable for the purposes of this invention are the alkyl esters of α-mercaptopropionic acid, which may be prepared from α-chloropropionic acid and sodium thiosulfate according to the procedure described in U.S. Pat. No. 2,413,361, which is incorporated herein by reference.

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