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Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets
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Abstract
The synthesis of racemic 3-(2-methoxyphenoxy)-1,2-propanediol (guaifenesin), an expectorant found in well-known cough syrups such as Benylin, is undertaken by a Williamson ether synthesis reaction. The same compound is simultaneously isolated and characterized from commercially available Guai-Aid cough tablets. The experiment is well-suited towards the introductory part of an advanced organic laboratory course and complements typical lecture topics in a stimulating manner. Consideration is given towards reaction mechanisms, stereochemistry, optical activity, pharmaceutical synthesis, and spectroscopic analysis. Discussion of the merits or disadvantages of marketing a drug as a racemic mixture, with reference to the notorious thalidomide case study, and the concept of enantioselective synthesis is possible.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Feature):
The Microscale LaboratoryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
Chirality / Optical ActivityCiting Articles
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
The Conversion of l-Phenylalanine to (S)-2-Hydroxy-3-phenylpropanoic Acid: A Simple, Visual Example of a Stereospecific SN2 Reaction
Nanine A. Van Draanen and Stephanie HengstJournal of Chemical Education2010 87 (6), 623-624The Conversion of l-Phenylalanine to (S)-2-Hydroxy-3-phenylpropanoic Acid: A Simple, Visual Example of a Stereospecific SN2 Reaction
Nanine A. Van Draanen and Stephanie HengstJournal of Chemical Education2010 87 (6), 623-624We report a simple, inexpensive, visual, and environmentally friendly SN2 reaction appropriate for the second-year organic chemistry laboratory that illustrates stereospecificity, dependence of water solubility on the state of ionization, optical activity,...
Microscale Synthesis of Chiral Alcohols via Asymmetric Catalytic Transfer Hydrogenation
Dirk De Vos , Christine M. Peeters and Rik DelieverJournal of Chemical Education2009 86 (1), 87Microscale Synthesis of Chiral Alcohols via Asymmetric Catalytic Transfer Hydrogenation
Dirk De Vos , Christine M. Peeters and Rik DelieverJournal of Chemical Education2009 86 (1), 87Synthesis of pure enantiomers is a key issue in industry, especially in areas connected to life sciences. Catalytic asymmetric synthesis has emerged as a powerful and practical tool. Here we describe an experiment on racemic reduction and asymmetric ...
Convenient Microscale Synthesis of a Coumarin Laser Dye Analog
Evangelos Aktoudianakis and Andrew P. DicksJournal of Chemical Education2006 83 (2), 287Convenient Microscale Synthesis of a Coumarin Laser Dye Analog
Evangelos Aktoudianakis and Andrew P. DicksJournal of Chemical Education2006 83 (2), 287The expeditious Knoevenagel synthesis of 3-acetyl-7-(diethylamino)-2H-1-benzopyran-2-one, a fluorescent coumarin laser dye analog, is described. This experiment is suitable for inclusion in mid-level undergraduate organic chemistry laboratories. The ...
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- Received: August 03, 2009
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