Acid catalyzed reaction of formaldehyde with 1-butene in acetic acid solution yields 2-methyltetrahydrofuran, 4-ethyl-l, 3-dioxane and both trans- and cis-4-acetoxy-3-methyltetrahydropyran as major products.
Ttans- and cis-isomers of tetrahydropyran derivative were separated each other by repeated gaschromatography, and the conformations of these compounds were investigated by proton magnetic resonance.