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Molecules 2012, 17(1), 571-583; doi:10.3390/molecules17010571
Article

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

1,2,* , 3, 2 and 1
Received: 14 November 2011; in revised form: 30 December 2011 / Accepted: 4 January 2012 / Published: 9 January 2012
(This article belongs to the Section Organic Synthesis)
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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 α,α-bis-(substituted-benzylidene)cycloalkanones were obtained. Aliphatic aldehydes also provided α,α-bis-(substituted-alkylidene)cycloalkanones in very good yields with minor amounts of a-(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.
Keywords: Claisen-Schmidt reaction; crossed-aldol reaction; cycloalkanone; solvent free Claisen-Schmidt reaction; crossed-aldol reaction; cycloalkanone; solvent free
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Rahman, A.F.M.M.; Ali, R.; Jahng, Y.; Kadi, A.A. A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones. Molecules 2012, 17, 571-583.

AMA Style

Rahman AFMM, Ali R, Jahng Y, Kadi AA. A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones. Molecules. 2012; 17(1):571-583.

Chicago/Turabian Style

Rahman, A. F. M. Motiur; Ali, Roushown; Jahng, Yurngdong; Kadi, Adnan A. 2012. "A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones." Molecules 17, no. 1: 571-583.



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