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ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
Published monthly
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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)
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