O.P([O-])([O-])(O)=O.[Na+].[Na+].OO.[Cl-].[Na+].[Cl:13][C:14]1[C:23]([CH:24]=[O:25])=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].Cl.S([O-])(O)=[O:32].[Na+]>O.C(#N)C>[Cl:13][C:14]1[C:23]([C:24]([OH:32])=[O:25])=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]
At 5° C., 13.8 g (0.11 mol) of sodium hydrogen phosphate monohydrate in 170 ml of water, 49.3 g (0.43 mol) of a 30% strength solution of hydrogen peroxide and 66.2 g (0.59 mol) of an 80% strength aqueous sodium chloride solution were added successively to a solution of 115.3 g (0.42 mol) of methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate and 2000 ml of acetonitrile. The reaction solution was subsequently stirred at 5° C. for 1 hour and then at room temperature for 12 hours. The pH was then adjusted to 1 using 10% strength hydrochloric acid, and 1500 ml of aqueous 40% strength sodium hydrogen sulfite solution were added. The mixture was stirred at room temperature for 1 hour and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with sodium hydrogen sulfite solution and dried. The solvent was distilled off, yielding 102.0 g of methyl 2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate.
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