Hydrochloric Acid → 6,12-Dithiatetradecanoic acid

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Sodium hydroxide (1M, 6.2 mL, 6.2 mmol) was added to a solution of ethyl 6,12-dithiatetradecanoate (0.9 g, 3.1 mmol) in MeOH (15 mL). After stirring for 4 hours, water (20 mL) was added and the reaction mixture was acidified (pH 1, HCl) extracted with EtOAc (2×100 mL), and the organic phase was washed with water (20 mL ), brine (20 mL ), and then dried (Na2SO4). The product crystallized from n-hexane to yield the title compound as a white solid (0.77 g, 95%, mp 49.5°-50.0° C). IR: 3000, 1720 cm-1 ; 1H NMR, 1.23 (t, 3H), 1.49 (quintet, 2H), 1.56-1.68 (m, 6H), 1.74 (quintet, 2H:), 2.38 (t, 2H), 2.51 (t, 2H), 2.53 (t, 4H), 2.54 (q, 2H), and 10.45 (b, 1H). Anal. Calcd for C12H24S2O2 : C, 54.50; H, 9.15%. Found: C, 54.59; H, 9.21%.

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