4-Chlorobenzenesulfonyl chloride → 8-(4-Chlorobenzenesulphonamido)-octanoic acid

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Reaction Steps

A solution of 4-chlorobenzenesulphonyl chloride (6 mmol) in chloroform (2.5 ml) was added to a solution of 8-aminooctanoic acid (6 mmol) in 10% sodium hydroxide solution (10 ml). The mixture was stirred at room temperature for 24 hours and was then extracted with chloroform (4×40 ml), the chloroform layers being discarded. The aqueous layer was acidified to pH1 with conc. HCl and was extracted with chloroform (4×100 ml). The combined chloroform extracts were then dried (Mg SO4). Concentration and crystallisation from isopropanol-water gave 8-(4-chlorobenzenesulphonamido)-octanoic acid (1.22 g; 58%); m.p. 122°-124° C.

Provenance & Evidence