The reaction of lead tetra-acetate with some acyclic hydroxy-ethers

Abstract

By means of lead tetra-acetate in refluxing benzene open-chain 1,2-, 1,3-, 1,4- and 1,5-hydroxy-ethers are mainly converted to the corresponding five-membered or six-membered cylic products. Thus, 2-alkoxy-1-ethanols afford 2-substituted 1,3-dioxolanes in 50-53% yield and 4-ethoxy-1-butanol gives 2-ethoxytetrahydrofuran in 52% yield; 3-alkoxy-1-propanols are oxidized to the corresponding 2-substituted 1,3-dioxans in 26-40% yield and 5-ethoxy-1-pentanol cyclizes to 2-ethoxytetrahydropyran in 46% yield. 2-Phenoxyethanol undergoes ring closure to 1,4-benzodioxan in 15% yield.