Alkylation of phenols with bifunctional compounds - Communication 17. Haloalkylation of cresols with 1,3-dibromopropane and 1,5-dichloropentane

Article abstract of DOI:10.1007/BF00915670

1. A study was made of the haloalkylation of cresols with 1,3-dibromopropane and 1,5-dichloropentane. The reaction goes in the presence of metallic copper at the boiling point of the halides, and does not go in the presence of acid catalysts (phosphoric acid, zinc chloride deposited on aluminum oxide). 2. Depending on the structure of the dihalide, the haloalkylation of cresols with dihaloalkanes goes either as O-haloalkylation (with the formation of the chloroalkyl ethers of the cresols when using 1,5-dichloropentane), or as cycloalkylation (with the formation of 6-methylchroman when using 1,3-dibromopropane).