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Acetals and Ethers. XVIII. Reaction Products of Prop-2-enal and But-2-enal with Mixture: n-Aliphatic Alcohol and Ethylene Glycol
Plasecki, Andrzej
, p. 579 - 586 (2007/10/02)
The direct condensation reaction of prop-2-enal or but-2-enal with mixture of n-aliphatic alcohol and ethylene glycol, in the presence of p-toluenesulphonic acid as catalyst, leads to a complex mixture of saturated, unsaturated, cyclic and linear acetals, moreover, 2-(2-alkoxy-alkyl)-1,3-dioxolanes are the main reaction products.The detailed investigations for n-butanol showed that unsaturated cyclic acetals: 2-vinyl-1,2-dioxolane 1a or 2-(1-propenyl)-1,3-dioxolane 1b, as well as unsaturated linear acetals: 1,1-dibutoxy-prop-2-en 2a or 1,1-dibutoxy-but-2-en 2b are intermediate reaction products.Additionally, it was found in final products presence of eight by-products: 5-butoxy-4a or 5-butoxy-7-methyl-1,4-dioxepane 4b, 1,1,3-tributoxypropane 5a or 1,1,3-tributoxybutane 5b, 2--6a or 2--1,3-dioxolane 6b, 5-(2-hydroxyethoxy)-7-methyl-1,4-dioxepane 7b, 1,3-dibutoxy-1-(2-hydroxyethoxy)-propane 8a or 1,3-dibutoxy-1-(2-hydroxyethoxy)-butane 8b, 1,1-dibutoxy-3-(2-hydroxyethoxy)-propane 9a or 1,1-dibutoxy-3-(2-hydroxyethoxy)-butane 9b, 3-butoxy-1,1-bis-(2-hydroxyethoxy)-propane 10a or 3-butoxy-1,1-bis-(2-hydroxyethoxy)-butane 10b, and 1-butoxy-1,3-bis-(2-hydroxyethoxy)-propane 11a or 1-butoxy-1,3-bis-(2-hydroxyethoxy)-butane 11b, respectively.
