A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones
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 aldehyd...
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/17/1/571/ |
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doaj-9024dbaad3954f8b80052f31b054cb4b2020-11-24T23:55:20ZengMDPI AGMolecules1420-30492012-01-0117157158310.3390/molecules17010571A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanonesYurngdong JahngA. F. M. Motiur RahmanRoushown AliAdnan A. KadiSolvent-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.http://www.mdpi.com/1420-3049/17/1/571/Claisen-Schmidt reactioncrossed-aldol reactioncycloalkanonesolvent free |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Yurngdong Jahng A. F. M. Motiur Rahman Roushown Ali Adnan A. Kadi |
| spellingShingle |
Yurngdong Jahng A. F. M. Motiur Rahman Roushown Ali Adnan A. Kadi A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones Molecules Claisen-Schmidt reaction crossed-aldol reaction cycloalkanone solvent free |
| author_facet |
Yurngdong Jahng A. F. M. Motiur Rahman Roushown Ali Adnan A. Kadi |
| author_sort |
Yurngdong Jahng |
| title |
A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones |
| title_short |
A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones |
| title_full |
A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones |
| title_fullStr |
A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones |
| title_full_unstemmed |
A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones |
| title_sort |
facile solvent free claisen-schmidt reaction: synthesis of α,α′-bis-(substituted-benzylidene)cycloalkanones and α,α′-bis-(substituted-alkylidene)cycloalkanones |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2012-01-01 |
| description |
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. |
| topic |
Claisen-Schmidt reaction crossed-aldol reaction cycloalkanone solvent free |
| url |
http://www.mdpi.com/1420-3049/17/1/571/ |
| work_keys_str_mv |
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