S. M. Trister, H. Hibbert
Dec 1, 1936
Citations
0
Influential Citations
10
Citations
Journal
Canadian journal of research
Abstract
The condensation of propionaldehyde, isobutyraldehyde, trimethylacetaldehyde and dibromoacetaldehyde with glycerol has been carried out in the presence of a catalyst (40% sulphuric acid) at 90 °C., and the resulting products have been shown to consist in each case of a mixture of the five- and six-membered cyclic acetals. The separation of these isomers from the acetal mixture was rendered possible by the difference in the physical properties of their benzoates. The structure of the latter was proved by saponification, methylation, hydrolysis and isolation of the resulting glycerol α- and glycerol β-methyl ethers respectively.With the isomers from dibromoacetaldehyde this method could not be used, owing to the labile character of the bromine atoms in presence of alkali. Their structures were proved by direct synthesis of the five-membered acetal benzoate from glycerol α-benzoate and dibromoacetaldehyde.The data obtained provide additional evidence of the marked influence exerted by the polar character of ...