Thioglycolic Acid → Hexyl mercaptoacetate

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Thioglycolic acid obtained from Evans Chemetics, Inc. (75 ml, 1.0785 mole) was added dropwise to hexanol obtained from Continental Oil Company (135.6 ml, 1.0785 mole) with 12% Dowex cation exchange resin 50W×12 50/100 (12% cross-linking, 13.2 g) as a catalyst. The solution was stirred and a nitrogen atmosphere maintained. The mixture was thereafter heated, and the byproduct, water, was distilled over as an azeotrope with hexanol at 95° C. and collected. A 10 ml excess of hexanol was added to the reaction mixture to replace that lost in the azeotrope. After 2.5 hours, an 89% yield was obtained. A vacuum of 60 mm Hg was then applied to further the reaction without increasing the temperature. After an additional hour, a 95.9% yield of hexyl thioglycolate was obtained.

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