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

Rahman, A. F. M. Motiur; Ali, Roushown; Jahng, Yurngdong; Kadi, Adnan A.

doi:10.3390/molecules17010571

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

by

A. F. M. Motiur Rahman

^1,2,*

,

Roushown Ali

³,

Yurngdong Jahng

² and

Adnan A. Kadi

¹

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh11451, Saudi Arabia

²

College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Korea

³

Department of Chemistry, College of Science, King Saud University, Riyadh 11451, Saudi Arabia

^*

Author to whom correspondence should be addressed.

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

Submission received: 14 November 2011 / Revised: 30 December 2011 / Accepted: 4 January 2012 / Published: 9 January 2012

(This article belongs to the Section Organic Chemistry)

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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

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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. https://doi.org/10.3390/molecules17010571

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. https://doi.org/10.3390/molecules17010571

Chicago/Turabian Style

Rahman, A. F. M. Motiur, Roushown Ali, Yurngdong Jahng, and Adnan A. Kadi. 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. https://doi.org/10.3390/molecules17010571

APA Style

Rahman, A. F. M. M., Ali, R., Jahng, Y., & Kadi, A. 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(1), 571-583. https://doi.org/10.3390/molecules17010571

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

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