Selectivity in Alkylation of Phenols with 1-Bromo-3-chloropropane Using Phase-Transfer Catalysis

Abstract

The use of various phase-transfer catalysts in the alkylation of phenol and substituted phenols with 1-bromo-3-chloropropane was investigated. When a quarternary ammonium salt of the general formula R′4N+ X-, where R′ = alkyl with a minimum chain length of 4 was used, a mixture of 1-aryloxy-3-chloropropane and 1-aryloxy-3-bromopropane resulted. The effect of counterion, added potassium bromide, and catalysts other than quarternary ammonium salts were assessed for the halopropylation of 2,5-dimethylphenol.