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A simple and efficient synthesis of 3-substituted derivatives of pentane-2,4-dione

Bartosz Staniszewski and Włodzimierz Urbaniak

Faculty of Chemistry, Adam Mickiewicz University, ul. Grunwaldzka 6, 60-780 Poznań, Poland

 

E-mail: wlodzimierz.urbaniak@amu.edu.pl

Received: 22 April 2008  Revised: 7 September 2008  Accepted: 22 September 2008

Abstract: A novel and efficient method of synthesis of 3-substituted derivatives of pentane-2,4-dione is proposed, wherein cheaper and easily accessible chloro derivatives are conversed into more reactive iodo derivatives. The method is based on the Finkelstein reaction for which the literature suggests highly polar organic solvents as ideal reaction media. In the presented work, the use of industrially used ketones, especially methyl isobutyl ketone, is proposed. The use of MIBK as a solvent additionally allows an azeotropic removal of water from the reaction mixture, enabling the application of moisture sensitive alkylating agents i.e. (3-chloropropyl)trimethoxysilane. The obtained products are isolated through distillation, which does however not allow the separation of C-alkylation products from O-alkylation ones. The products not containing water-sensitive substituents were isolated as copper complexes. The pure product of C-alkylation was obtained by decomposition of the copper complex with a hydrochloric acid solution and extraction of the formed ligand to an organic phase i.e. hexane. The obtained ligand can be further purified by distillation.

Keywords: beta-diketones - acetylacetone derivatives -  C-alkylation - methyl isobutyl ketone

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-008-0097-9

 

Chemical Papers 63 (2) 212–216 (2009)

Thursday, April 09, 2020

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