C1(C)C=CC=CC=1.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[S:13][CH2:14][CH2:15][C:16]([OH:18])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+]>C(OCC)(=O)C.CCCCCC.O>[S:8]1[C:9]2[S:13][CH2:14][CH2:15][C:16](=[O:18])[C:10]=2[CH:11]=[CH:12]1In a 2-L reactor fitted with an overhead mechanical stirrer, thermometer, addition funnel, reflux condenser, and nitrogen bubbler vented through an acid-vapor scrubber was placed the toluene solution of product from Step A (130.7 g, 695 mmol). The reaction mixture was brought to an initial temperature of 20° C. and trifluoroacetic anhydride (161 g, 765 mmol) was added over 5 minutes to the stirred solution. The reaction was then heated to 35°-38° C. and stirred for about 1.5 hours. The reaction mixture was then slowly added to water (500 mL) maintaining the temperature at <25° C. A pH probe was placed in the vessel and the mixture was titrated to pH 7.0 with 50% sodium hydroxide (123 g, 1.53 mole). The layers were separated and the aqueous phase was extracted once with toluene (200 mL), The combined organic extracts were then concentrated under vacuum (43 mBar) to a volume of 200 mL and then diluted to 1.2 L with ethyl acetate for the next step (oxidation). A small sample was chromatographed to obtain the following data: Rf =0.29 (85:15 hexane:ethyl acetate). m.p. 61°-62° C. 1H NMR: δ 7.42 (d, J=5.4, H2); 6.98 (d, J=5.4 H3); 3.33 (m, C5H2); 2.82 (m, C6H2). 13C NMR; δc 188.9 (C4), 150.9, 135.0 (C3a, C7a), 126.1, 121.8 (C2, C3), 38.1 (C6), 30.0 (C5). Anal Calcd for C7H6OS2 : C, 49.39; H, 3.55; S, 37.66. Found: C, 49.56; H, 3.58; S, 37.68.
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