Die Reaktion von 1,2-Epoxy-octan mit 2-Dimethylamino-äthanol

2-Dimethylaminoethanol reacts with 1,2-epoxyoctane presumably via a hydrogen-bonded complex to form a quaternary ammonium compound which exhibits a fair stability at lower temperatures. At higher temperatures the quaternary structure decomposes with the resulting formation of a wide variety of products. Most of the products have been identified and a reasonable mechanistic picture for their formation is presented. The main products of the reaction are 1-(ß-dimethylaminoethoxy)-2-octanol (IIIa) and 1-dimethylamino-2-octanol (IV), the latter being formed according to several pathways concurrently with ethylene oxide, 2-methyl-4-hexyl-1, 3-dioxolane (VI), and 2-hexyl-1, 4-dioxane (VII). Some of the higher molecular weight products are secondary products resulting from the action of epoxide on the primary reaction products IIIa and IV. The relative amount of each product formed depends on the ratio of starting materials and reaction temperature. In the presence of an additional hydroxylic solvent such as ethanol, the solvent enters also into the reaction.