ELECTROCHEMICAL REACTIONS OF HALOHYDRINS .1. ATTEMPT AT REDUCTIVE COUPLING

The electrochemical reductive coupling of 2-chloroethanol and 2-bromoethanol to 1,4-butanediol was attempted. The electrochemical cleavage of the carbon-halogen bond leads to intermediates which are either unstable and decompose to ethylene and OH-, or undergo chemical reactions leading to ether formation. The presence of the hydroxyl group in halohydrins seems to be responsible for the observed reaction paths. When the alcohol group was protected by esterification, coupled products were observed. Coupling of bromoethyl acetate to 1,4-butanediol diacetate thus appears technically feasible, but is a commercially less attractive route to 1,4-butanediol. © 1978 Chapman and Hall Ltd.