4-Hydroxybenzenesulfonicacid,disodiumsalt → Nonanoic acid, 2-chloro-, 4-sulfophenyl ester, sodium salt

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Reaction Steps

Anhydrous disodium p-phenolsulfonate (28.5 g; 0.130 mole) and 30.3 g (0.1436 mole) of 2-chlorononanoyl chloride were combined in a 500 ml round-bottomed flask. The flask was then immersed in an oil bath which had been preheated to 110° C. Within five minutes an exothermic reacting occurred which caused the entire mixture to congeal. After cooling, the mixture was triturated three times with 150-200 ml portions of ether and the product was vacuum dried. Elemental and nmr analyses of the resulting tan powder, 46.2 g, indicated that it was composed of 11.5% NaCl, 17.7% disodium p-phenolsulfonate, and 70.8% of sodium p-(2-chlorononanoyloxy)benzene sulfonate. This represents a 68% yield of the desired product.

Provenance & Evidence