A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of alpha,alpha '-bis-(Substituted-benzylidene)cycloalkanones and alpha,alpha '-bis-(Substituted-alkylidene)cycloalkanones

Title
A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of alpha,alpha '-bis-(Substituted-benzylidene)cycloalkanones and alpha,alpha '-bis-(Substituted-alkylidene)cycloalkanones
Author(s)
장영동A.F.M. 모티울 라만[A.F.M. 모티울 라만]라우쇼운 알리[라우쇼운 알리]Adnan A. Kadi[Adnan A. Kadi]
Keywords
CROSS-ALDOL CONDENSATION; ALPHA,ALPHA'-BIS(SUBSTITUTED BENZYLIDENE) CYCLOALKANONES; AROMATIC-ALDEHYDES; IONIC LIQUID; MICROWAVE IRRADIATION; BIOLOGICAL EVALUATION; CONVENIENT SYNTHESIS; EFFICIENT SYNTHESIS; KETONES; BENZYLIDENE)CYCLOALKANONES
Issue Date
201201
Publisher
MDPI AG
Citation
MOLECULES, v.17, no.1, pp.571 - 583
Abstract
Solvent-free Claisen-Schmidt reactions of cycloalkanones with various substituted benzaldehydes (aryl aldehydes) using solid NaOH (20 mol%) and applying a grinding technique were studied. Quantitative yields (96-98%) of alpha,alpha'-bis-(substituted-benzylidene)cycloalkanones were obtained. Aliphatic aldehydes also provided alpha,alpha'-bis-(substituted-alkylidene)cycloalkanones in very good yields with minor amounts of alpha-(substituted-alkylidene)cycloalkanones. The catalytic performance of solid NaOH was examined. The molar ratio of NaOH was optimized. The catalytic effect of solid NaOH was also evaluated by comparing it with KOH, NaOAc, and NH4OAc and it turns out that 20 mol% of solid NaOH was good enough to catalyze the Claisen-Schmidt reactions of cycloalkanones with various substituted benzaldehydes. Additionally, the regioselectivity of the Claisen-Schmidt reaction of acetone with benzaldehyde was examined. Using the same method, we could synthesize the corresponding bis-benzylidene- and mono-benzylideneacetone separately in 98% and 96% yields, respectively.
URI
http://hdl.handle.net/YU.REPOSITORY/29993http://dx.doi.org/10.3390/molecules17010571
ISSN
1420-3049
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약학대학 > 약학부 > Articles
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