Chlorination of toluene by two-phase electrolysis

Abstract

The electrochemical chlorination of aromatic compounds is of interest from two standpoints; the development of new practical processes and understanding the mechanism of many electrochemical oxidations. The electro-chlorination of toluene has been attempted by many workers. Gourcy et al. [1], for instance, carried out the anodic chlorination of toluene in CH3CN containing some Lewis acids and obtained oand p-chlorotoluenes. We [2] have also obtained chlorotoluenes with high yields through the electrolysis of toluene in CH3OH/LiC1. However, no chloroderivatives substituted in the methyl group have been reported as formed by electrochemical methods. Forsyth and Pletcher [3] have discussed Xwo-phase electrolysis' as an advantageous technology in practical organic electrosynthesis. However, we wish to show that two-phase electrolysis can yield different products from conventional homogeneous electrolysis. In the present work, we have obtained benzyl chloride as well as chlorotoluenes by the electrolysis of toluene in immiscible two-phase systems (Scheme 1).