Conversion of Alkyl Halides into the Corresponding Alcohols Under Mild Reaction Conditions

Clare L. Ruddick; Philip Hodge; Mark P. Houghton

doi:10.1055/s-1996-4395

Synthesis 1996; 1996(11): 1359-1362
DOI: 10.1055/s-1996-4395

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Conversion of Alkyl Halides into the Corresponding Alcohols Under Mild Reaction Conditions

Clare L. Ruddick, Philip Hodge^* , Mark P. Houghton

^*Chemistry Department, University of Manchester, Manchester M13 9PL, UK

Abstract

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Reaction of primary, cyclopentyl, allyl and arylmethyl halides, but not an acyclic secondary halide or a tertiary halide, in acetone or tetrahydrofuran with the formate form of a commercial anion-exchange resin gave formate esters in good yields. The formates were hydrolysed efficiently to the corresponding alcohols by a brief treatment with hydrochloric acid. Reaction of primary alkyl bromides or iodides, secondary alkyl bromides, cinnamyl and arylmethyl halides in tetrahydropyran or 1,4-dioxane with the bicarbonate form of the same anion-exchange resin gave the corresponding alcohols directly in good yields. This latter reaction can be carried out successfully in the presence of ester or amide groups.

polymer-supported bicarbonate - polymer-supported formate - hydrolysis

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