Synthesis of 4-Chlorocyclohexene and Reaction of 4-Chlorocyclohexene with Aqueous Sulfuric Acid

Abstract

Synthesis of 4-chlorocyclohexene from 1, 4-cyclohexadiene and hydrogen chloride was investigated. And reaction of 4-chlorocyclohexene with aqueous sulfuric acid was carried out and the products were investigated.When hydrogen chloride was bubbled through the reaction mixture consisting of 1, 4-cyclohexadiene 6.0 g, zinc chloride 0.6 g, and glacial acetic acid 4.5 g at 20°C for seven hours, the products were 4-chlorocyclohexene (75%), dichlorocyclohexanes (21%) and 1, 4-cyclohexadiene (4%).When 4-chlorocyclohexene reacted with 65% sulfuric acid at 60°C for four hours, the products were mainly cis- and trans-isomers of 3-and 4-chlorocyclohexanols (yield 74 mol%), accompanied by small amounts of sulfates of chlorocyclohexanols, dichlorocyclohexanes and phenylcyclohexane.Phenylcyclohexane and dichlorocyclohexanes were the main products when the reaction was carried out at 100°C with 60% Sulfuric acid.