p-Toluenesulfonic acid → Toluenesulfonate

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In a preferred embodiment, a mixture containing an 11a-halo-6-deoxy-6-demethyl-6-methylenetetracycline, preferably the p-toluene sulfonate of 11a-chloro methacycline; hydridotetrakis(triphenylphosphine) rhodium (I); and a tertiary phosphine, preferably triphenylphosphine, in methanol is subjected to agitation in a stainless steel autoclave, and hydrogenated at about 50° to 90° C. under a pressure between about 4 and 12 kg/cm2, prior to the termination of the reaction. Sulfosalicylic acid is added and the reaction mixture is cooled to about 10° C. for 2-4 hours. The alpha-6-deoxy-5-oxytetracyline sulfosalicylate, preferably doxycyline sulfosalicylate (or toluene sulfonate) thus obtained is filtered and washed with methanol.

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