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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > February  >
In the Laboratory
Synthesis of Methyl Diantilis, a Commercially Important Fragrance
William H. Miles and Katelyn B. Connell
Department of Chemistry, Lafayette College, Easton, PA 18042
Cover
February 2006
Vol. 83 No. 2
p. 285
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.

Supplement
Instructions for the students and notes for the instructor are available. (Updated June 2006.)
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Citation
Miles, William H.; Connell, Katelyn B. J. Chem. Educ. 2006, 83, 285.
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Keywords
Alcohols; Catalysis; Ethers; Food Science; Hands-On Learning / Manipulatives; Industrial Chemistry; IR Spectroscopy; Laboratory Instruction; Lewis Acids / Bases; NMR Spectroscopy; Organic Chemistry; Oxidation / Reduction; Second-Year Undergraduate; Synthesis
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History
Created:
Last Updated:
1/5/2006
6/10/2008
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