Formation of Bis(3,5-dichloro-4-hydroxyphenyl)methane From the Reduction of 3,5-Dicholo-4-hydroxybenzoic acid

Abstract

This research was aimed to reduce 3,5-dicholo-4-hydroxybenzoic acid to 3,5-dicholo-4-hydroxybenzyl alcohol by using LiAlH₄ as catalyst. Unfortunately, the main product found was different from the normal reduction of carboxylic acid. The obtained product is bis(3,5-dichloro-4-hydroxyphenyl)methane  which formed from the cross-linking of the acid. The structure elucidation was carried out based on the spectroscopic analysis method (H-NMR, C-NMR IR, GC-MS). The product, bis(3,5-dichloro-4-hydroxyphenyl)methane, identified as a brown crystaline solid in 52 % yield.

Keywords: bis(3,5-dichloro-4-hydroxyphenyl)methane, 3,5-dicholo-4-hydroxybenzoic acid, LiAlH₄