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Synthesis of Aspirin: A General Chemistry Experiment

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John A. Olmsted III

Department of Chemistry and Biochemistry, California State University, Fullerton, Fullerton, CA 92834

J. Chem. Educ., 1998, 75 (10), p 1261

DOI: 10.1021/ed075p1261

Publication Date (Web): October 1, 1998

Section:

History, Education, and Documentation

Abstract

An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. It is the two-step synthesis of aspirin starting from oil of wintergreen. The mechanism for this synthesis provides examples of three major classes of chemical reactions: hydrolysis, condensation, and proton transfer. To understand the chemistry, the student must be able to recognize the common molecular framework shared by oil of wintergreen, salicylic acid, and aspirin and to identify the -OH and -CO₂ sites where chemical changes occur. The experiment differs in three ways from traditional aspirin synthesis experiments for general chemistry. It is designed to be performed early rather than late; it starts from a naturally occurring material and requires two steps rather than one; and it utilizes FTIR spectroscopy to distinguish among oil of wintergreen starting material, salicylic acid intermediate, and aspirin product. The use of FTIR spectroscopy introduces students to a modern analytical technique that is currently used in research involving aspirin.

Keywords (Audience):

First-Year Undergraduate / General

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Drugs / Pharmaceuticals

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This article has been cited by 6 ACS Journal articles (5 most recent appear below).

Prediction of log P: ALOGPS Application in Medicinal Chemistry Education
Jacek Kujawski, Marek K. Bernard, Anna Janusz, and Weronika Kuźma
Journal of Chemical Education2012 89 (1), 64-67
- Prediction of log P: ALOGPS Application in Medicinal Chemistry Education
  Jacek Kujawski, Marek K. Bernard, Anna Janusz, and Weronika Kuźma
  Journal of Chemical Education2012 89 (1), 64-67
  Molecular hydrophobicity (lipophilicity), usually quantified as log P where P is the partition coefficient, is an important molecular characteristic in medicinal chemistry and drug design. The log P coefficient is one of the principal parameters for the ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Using Aspirin as a Teaching Tool
Liana Lamont
Journal of Chemical Education2009 86 (4), 476
- Using Aspirin as a Teaching Tool
  Liana Lamont
  Journal of Chemical Education2009 86 (4), 476
  Offers a list of JCE instructional resources related to aspirin.
  Abstract | Hi-Res PDF | PDF w/ Links
Preparation of Oil of Wintergreen from Commercial Aspirin Tablets. A Microscale Experiment Highlighting Acyl Substitutions
Aaron M. Hartel and James M. Hanna Jr.
Journal of Chemical Education2009 86 (4), 475
- Preparation of Oil of Wintergreen from Commercial Aspirin Tablets. A Microscale Experiment Highlighting Acyl Substitutions
  Aaron M. Hartel and James M. Hanna Jr.
  Journal of Chemical Education2009 86 (4), 475
  A single-pot procedure for the preparation of methyl salicylate (oil of wintergreen) from commercial aspirin tablets has been developed. The synthesis proceeds via a tandem transesterification–Fischer esterification using acidic methanol and can be ...
  Abstract | Hi-Res PDF | PDF w/ Links
The Science Teacher: Spring 2006
Steve Long
Journal of Chemical Education2006 83 (6), 830
- The Science Teacher: Spring 2006
  Steve Long
  Journal of Chemical Education2006 83 (6), 830
  This article reviews chemistry-related articles published in The Science Teacher between September 2005 and February 2006. Lab safety, inquiry-based activities, flame tests, designing safe lab facilities, interdisciplinary chemistry teaching, ...
  Abstract | Hi-Res PDF | PDF w/ Links
A Greener Approach to Aspirin Synthesis Using Microwave Irradiation
Ingrid Montes , David Sanabria , Marilyn García , Joaudimir Castro and Johanna Fajardo
Journal of Chemical Education2006 83 (4), 628
- A Greener Approach to Aspirin Synthesis Using Microwave Irradiation
  Ingrid Montes , David Sanabria , Marilyn García , Joaudimir Castro and Johanna Fajardo
  Journal of Chemical Education2006 83 (4), 628
  Microwave irradiation provides a way for flash heating as an alternative to standard thermal heating in chemical reactions. This technology has been employed to drastically reduce reaction times and even modify selectivity. In addition to this feature, ...
  Abstract | Hi-Res PDF | PDF w/ Links