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

E. Reinholz; A. Becker; B. Hagenbruch; S. Schäfer; A. Schmitt

doi:10.1055/s-1990-27096

Synthesis 1990; 1990(11): 1069-1071
DOI: 10.1055/s-1990-27096

paper

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

E. Reinholz^* , A. Becker, B. Hagenbruch, S. Schäfer, A. Schmitt

^*Boehringer Mannheim GmbH, Department of Chemical Development Sandhofer Straße 116, D-6800 Mannheim 31, Germany

Abstract

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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.

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