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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > November  >
In the Laboratory
Green Chemistry
Synthesis of meso-Diethyl-2,2′-dipyrromethane in Water. An Experiment in Green Organic Chemistry
Abilio J. F. N. Sobral
Department of Chemistry, University of Coimbra, Coimbra, Portugal
Cover
November 2006
Vol. 83 No. 11
p. 1665

Abstract
In this laboratory activity, students are introduced to the synthesis of dipyrromethanes, which are important precursors for porphyrin and calix[4]pyrrole. The acid-catalyzed condensation of pyrrole and 3-pentanone in water uses common inexpensive reagents and solvents to produce the meso-diethyl-2,2′-dipyrromethane in one step, in an analytical grade directly from the aqueous reaction medium.
Supplement
Detailed student procedures; postlab questions and answers; instructor notes with comments on the experiment; CAS numbers; extended hazards section; elemental analysis; MS; 1H NMR; FTIR; and X-ray results are available.
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Citation
Sobral, Abilio J. F. N. J. Chem. Educ. 2006 83 1665.
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Keywords
Aldehydes / Ketones; Aqueous Solution Chemistry; Green Chemistry; Hands-On Learning / Manipulatives; Laboratory Instruction; Organic Chemistry; Second-Year Undergraduate; Synthesis
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History
Created:
Last Updated:
9/19/2006
9/20/2006
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Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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