Semimicro/Microscale Adaptation of the Cobalt Chloride/Sodium Borohydride Reduction of Methyl Oleate

The reduction of alkenes usually involves a hydrogen source and a catalyst. This process is both expensive and not well-suited for a large teaching laboratory. This paper presents an alternative procedure using a mixture of cobalt chloride and sodium borohydride to achieve the reduction of methyl ol...

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Bibliographic Details
Published inJournal of chemical education Vol. 96; no. 4; pp. 772 - 775
Main Authors McKee, James R, Zanger, Murray, Chiariello, Carmine, McKee, James A, Dorfner, Walter, Fasella, Elisabetta, Koo, Yumee
Format Journal Article
LanguageEnglish
Published Easton American Chemical Society and Division of Chemical Education, Inc 09.04.2019
Division of Chemical Education, Inc
American Chemical Society
Subjects
Alkenes
Borohydrides
Catalysts
Chemistry
Cobalt
College Science
Laboratories
Laboratory Experiments
Laboratory Procedures
NMR spectroscopy
Reduction
Science Experiments
Science Instruction
Sodium
Spectroscopy
NMR Spectroscopy
Hands-On Learning/Manipulatives
Upper-Division Undergraduate
Oxidation/Reduction
Laboratory Instruction
Second-Year Undergraduate
Green Chemistry
Catalysis
Microscale Lab
Organic Chemistry
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Summary:The reduction of alkenes usually involves a hydrogen source and a catalyst. This process is both expensive and not well-suited for a large teaching laboratory. This paper presents an alternative procedure using a mixture of cobalt chloride and sodium borohydride to achieve the reduction of methyl oleate to methyl stearate. This procedure is safe, simple, and inexpensive. NMR spectroscopy is used as an analytical tool to determine the extent of the reduction.
ISSN:0021-9584
1938-1328
DOI:10.1021/acs.jchemed.8b00222