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Methylation of Isobutyrophenone Using Potassium Triphenylmethide: An Advanced Organic Chemistry Laboratory Experiment

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Fred J. Matthews

Department of Chemistry, Austin Peay State University , P.O. Box 4547, Clarksville, TN 37044

J. Chem. Educ., 1997, 74 (8), p 996

DOI: 10.1021/ed074p996

Publication Date (Web): August 1, 1997

Section:

History, Education, and Documentation

Abstract

This paper provides a detailed description of an alkylation reaction of isobutyrophenone using tritylpotassium as base. The reaction involves use of moisture sensitive reactants and intermediates under an inert atmosphere and is best suited for an advanced organic chemistry laboratory. Students have the opportunity to perform a variety of laboratory techniques (crystallization, distillations, extraction, chromatography, use of syringes for transfer of reagents) and instrumental methods (GLC, IR, GC/MS, H-1 NMR, C-13 NMR). The experimental section includes safety precautions regarding the required reagents, descriptions of the necessary glassware, purification and preparation of reagents and solvents, preparation of the base (potassium triphenylmethide), methylation of the ketone (isobutyrophenone), and separation and identification of the product (pivalophenone).

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Synthesis

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

A Practical New Chiral Controller for Asymmetric Diels−Alder and Alkylation Reactions
Georgios Sarakinos and E. J. Corey
Organic Letters1999 1 (11), 1741-1744
- A Practical New Chiral Controller for Asymmetric Diels−Alder and Alkylation Reactions
  Georgios Sarakinos and E. J. Corey
  Organic Letters1999 1 (11), 1741-1744
  The enantiomerically pure hydroxy sulfones (+)- and ()-2 have been prepared from 1,2-epoxycyclohexane by a simple and practical procedure. The acrylate esters of these alcohols undergo BCl3-catalyzed DielsAlder reactions with a variety of dienes at 78 ...
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