W. Miles, K. Connell
Feb 1, 2006
Citations
0
Influential Citations
30
Citations
Journal
Journal of Chemical Education
Abstract
This experiment describes the synthesis of a family of fragrances, including the commercially important Methyl Diantilis, that were covered by a U.S. patent in 1987. The first step in the synthesis is the reduction of 3-ethoxy-4-hydroxybenzaldehyde (ethyl vanillin) to 3-ethoxy-4-hydroxybenzyl alcohol (ethyl vanillyl alcohol). In the second step, etherification of 3-ethoxy-4-hydroxybenzyl alcohol yields 3-ethoxy-4-hydroxybenzyl methyl ether (Methyl Diantilis). Using either ethanol, 1-propanol, or 2-propanol in the etherification step yields the corresponding 3-ethoxy-4-hydroxybenzyl alkyl ethers, which also were described in the patent. All of the 3-ethoxy-4-hydroxybenzyl alkyl ethers have pronounced olfactive notes. This experiment also provided an excellent introduction to intellectual property laws.Procedure updated June 2008. See Letter re: this article.