On the Electrolytic Reduction of Tribromoresorcinol

Abstract

In the studies of halogen substituted resorcinols conducted by the Chemistry Department at Washinton and Lee University, considerable work was done by Lewis Daniel Williams on the preparation of 2-substituted resorcinols by reduction. The main purpose of Mr. Williams work was the improvement of the yield of a reaction reported by Davis and Harington [2] in which tribromoresorcinol was made to yield 2-Bromoresorcinol by alkaline reduction with sodium sulfite. Mr. Williams met with great success in his work but a new approach to this reduction was suggested by Mr. John Robert Taylor, to wit, the reduction of tribromoresorcinol by electrolysis in acid media because, first, alkaline solutions have a strong tendency to darken and yield tarry products as a side reaction, and secondly, because the usual mild reducing agents apparently only operate in alkaline media. [1] As a result of discussions with Mr. Taylor, it was decided to nduct this work along three lines. 1. To check agreement of electrolytic reduction if any, with Davis and Harrington's reduction mechanism. 2. To devise and attempt to perfect a new [electrolytic] reduction process to improve the yield of 2-bromoresorcinol and 2,4-dibromoresorcinol. 3. To attempt to carry the reduction all the way to resorcinol and correlate in some way the decomposition voltage, if reproducible, of each stage in the process in order to determine qualitatively the bond strength of the three bromine-carbon bonds. [From Introduction]