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Synthesis of Ethyl Salicylate Using Household Chemicals

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Sally Solomon , Chinhyu Hur , Alan Lee and Kurt Smith

Drexel University, Philadelphia, PA 19104

J. Chem. Educ., 1996, 73 (2), p 173

DOI: 10.1021/ed073p173

Publication Date (Web): February 1, 1996

Section:

History, Education, and Documentation

Abstract

Ethyl salicylate is synthesized, isolated, and characterized in a three-step process using simple equipment and household chemicals. First, acetylsalicylic acid is extracted from aspirin tablets with isopropyl alcohol, then hydrolyzed to salicylic acid with muriatic acid, and finally, the salicylic acid is esterified using ethanol and a boric acid catalyst. The experiment can be directed towards high school or university level students who have sufficient background in organic chemistry to recognize the structures and reactions that are involved.

Keywords (Audience):

High School / Introductory Chemistry

Keywords (Domain):

Organic Chemistry

Keywords (Feature):

Filtrates and Residues

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Synthesis

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Citing Articles

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

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
Using Ice-Cooled Condensers in Chemistry Laboratory
Sally Solomon , Bryan Brook , Susan Rutkowsky and Joseph Bennet
Journal of Chemical Education2003 80 (3), 299
- Using Ice-Cooled Condensers in Chemistry Laboratory
  Sally Solomon , Bryan Brook , Susan Rutkowsky and Joseph Bennet
  Journal of Chemical Education2003 80 (3), 299
  An ice-cooled condenser, consisting of a jacket built around a tube open to the atmosphere with an outlet for removal of melting ice, is designed for use in academic laboratory classes. The apparatus can be used in place of standard water cooled ...
  Abstract | Hi-Res PDF | PDF w/ Links
Experiments with Aspirin
Edward Barry , Londa L. Borer
Journal of Chemical Education2000 77 (3), 354
- Experiments with Aspirin
  Edward Barry , Londa L. Borer
  Journal of Chemical Education2000 77 (3), 354
  A series of experiments based on aspirin have been used in our high school chemistry laboratory. Experiments include (i) synthesis, purification, and characterization of aspirin by mp and TLC, (ii) percentage composition of a commercial aspirin tablet by ...
  Abstract | Hi-Res PDF | PDF w/ Links
Parallel Combinatorial Esterification: A Simple Experiment for Use in the Second-Semester Organic Chemistry Laboratory
David M. Birney and Stephen D. Starnes
Journal of Chemical Education1999 76 (11), 1560
- Parallel Combinatorial Esterification: A Simple Experiment for Use in the Second-Semester Organic Chemistry Laboratory
  David M. Birney and Stephen D. Starnes
  Journal of Chemical Education1999 76 (11), 1560
  Combinatorial chemistry has revolutionized the way potential new drugs are discovered. This simple experiment utilizes the Fischer esterification, a common reaction in second-semester organic laboratories, to demonstrate the fundamentals of combinatorial ...
  Abstract | Hi-Res PDF | PDF w/ Links