Hydrolysis of F-octanesulfinic acid

Abstract

F-alkanoic acids are useful functional fluorochemicals that can be produced in modest yields by electrochemical fluorination (ECF). In contrast, F-alkanesulfonyl fluorides, R fCF 2SO 2F, are readily available in good yields by the ECF method. The conversion of R fCF 2SO 2F to R fCO 2H is desirable under mild conditions. We have found that acid hydrolysis of F-octanesul finic acid, C 8F 17SO 2H, obtained by the reduction of the sulfonyl fluoride, C 8F 17SO 2F, with diluted mineral acids including 10% H 2SO 4, yielded primarily F-octanoic acid. Varying amounts of F-octanesul fonic acid, C 8F 17SO 3H, are also formed. The hydrolysis conditions are far milder than those used by Ma et al. (CA 96:6660u). Studies by Huang et al. (J. Fluor. Chem. (1983) 23, 229) have attributed desulfoxylation of the sul finic acid to a redox reaction. Our studies suggested that a hydrolysis rather than a redox reaction is taking place.