Prev. Article Next Article Table of Contents

Article

Synthesis of Methyl Diantilis, a Commercially Important Fragrance

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

William H. Miles and Katelyn B. Connell

Department of Chemistry, Lafayette College, Easton, PA 18042

J. Chem. Educ., 2006, 83 (2), p 285

DOI: 10.1021/ed083p285

Publication Date (Web): February 1, 2006

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Alcohols

View: Hi-Res PDF | PDF w/ Links

Citing Articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 2 ACS Journal articles (2 most recent appear below).

A Flexible Solvolysis Experiment for the Undergraduate Organic Laboratory
John J. Esteb , John R. Magers , LuAnne McNulty , Paul Morgan , Kathryn Tindell and Anne M. Wilson
Journal of Chemical Education2009 86 (7), 853
- A Flexible Solvolysis Experiment for the Undergraduate Organic Laboratory
  John J. Esteb , John R. Magers , LuAnne McNulty , Paul Morgan , Kathryn Tindell and Anne M. Wilson
  Journal of Chemical Education2009 86 (7), 853
  A simple SN1 reaction is presented that uses bromotriphenylmethane and a range of oxygen-based nucleophiles including water and various alcohols. This procedure represents a process that affords easy isolation of solid products. Typical student yields ...
  Abstract | Hi-Res PDF | PDF w/ Links
Modification to Synthesis of Methyl Diantilis
William H. Miles
Journal of Chemical Education2008 85 (7), 917
- Modification to Synthesis of Methyl Diantilis
  William H. Miles
  Journal of Chemical Education2008 85 (7), 917
  After we published the “Synthesis of Methyl Diantilis, a Commercially Important Fragrance,”we encountered a problem with the catalyst, Amberlyst-15, used in the second step. A revised laboratory procedure has replaced the original supplement available at ...
  Abstract | Hi-Res PDF | PDF w/ Links