[CH3:1][C:2]1[C:12]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].S(OOS([O-])(=O)=O)([O-])(=O)=[O:19].[K+].[K+]>FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CC1C=CC(C(C)C)=CC=1.CC1C=CC(C(C)C)=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[OH:19][C:9]1[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([CH3:1])[C:12]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][CH:10]=1
To a solution of ethyl 2-methyl-3-[(methylsulfonyl)oxy]benzoate (116b, 3.0 g, 12 mmol) in trifluoroacetic acid (35 mL) and trifluoroacetic anhydride (15 mL) was added potassium persulfate (3.5 g, 13 mmol) and dichloro(p-cymene)ruthenium(II) dimer (0.36 g, 0.59 mmol). The resulting mixture was stirred at 90° C. in a sealed tube for 22 hours. The reaction mixture was concentrated under vacuum then diluted with water (50 mL) and extracted with dichloromethane (2×75 mL). The combined organic layers were washed with brine (50 mL), dried over magnesium sulfate, concentrated under vacuum, and purified by column chromatography (40% EtOAc/Heptane) to give ethyl 6-hydroxy-2-methyl-3-[(methylsulfonyl)oxy]benzoate (116c, 1.3 g, 41% yield) as a white solid.
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