Process Development of the Weiss–Cook Reaction for the Preparation of cis-1,5-Dimethylbicyclo[3.3.0]octane-3,7-dione in the Undergraduate Organic Laboratory

Matthew Korman; Eric Paz; Tylor Franklin; Nicholas R. Lewandowski; Bethany Sullivan; Andrea M. Imhoff; Luke Fisher; Katherine A. Bichler; Scott G. Van Ornum

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Process Development of the Weiss–Cook Reaction for the Preparation of cis-1,5-Dimethylbicyclo[3.3.0]octane-3,7-dione in the Undergraduate Organic Laboratory

Matthew Korman ^[1] ; Eric Paz ^[1] ; Tylor Franklin ^[1] ; Nicholas R. Lewandowski ^[1] ; Bethany Sullivan ^[1] ; Andrea M. Imhoff ^[1] ; Luke Fisher ^[2] ; Katherine A. Bichler ^[1] ; Scott G. Van Ornum ^[1]
1. [1] Concordia University Wisconsin
  
  Concordia University Wisconsin
  
  City of Mequon, Estados Unidos
2. [2] Dotmatics, Inc., United States
Localización: Journal of chemical education, ISSN 0021-9584, Vol. 97, Nº 10, 2020, págs. 3835-3838
Idioma: inglés
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Resumen
- A four week laboratory experiment was designed on the basis of a modification of the Weiss–Cook reaction for the preparation of cis-1,5-dimethylbicyclo[3.3.0]octane-3,7-dione. In general, this very versatile organic reaction involves a two-step process reacting biacetyl with 2 mol of dimethyl-1,3-acetonedicarboxylate to form cis-bicycle([3.3.0]octane-3,7-dione). The reaction employs an aldol reaction followed by successive Michael reactions that are typically encountered near the end of a second-year undergraduate organic chemistry course. The students gained hands-on experience with 1H NMR and IR spectroscopy to analyze the intermediate and final product. Students wrote a formal laboratory report and discussed their results, including a proposal of the reaction mechanism and calculation of the overall yield. The experiment may be used in a traditional second semester organic chemistry laboratory or an advanced organic chemistry synthesis course on multigram or microscale levels.