Green synthesis of α-methylcinnamaldehyde via Claisen-Schmidt condensation of benzaldehyde with propanal over Mg–Zr mixed oxide supported on HMS

Wagh, Dipti P.; Yadav, Ganapati D.

doi:10.1016/j.mcat.2018.08.014

Cited by 12 publications

(6 citation statements)

References 34 publications

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“…Considering the significance of this synthesis strategy, several catalysts with certain desirable characteristics have been developed to date. − Even today, extensive research is being performed to improve the existing methods. In 2016, Yu et al reported using Ca(OH) 2 for the condensation of aldehydes and methyl ketones.…”

Section: Resultsmentioning

confidence: 99%

“…Since then, different synthetic methods have been developed by changing the catalyst, solvent system, or both. Some of the most efficient catalysts used for this transformation are metal- or metal oxide-based catalysts, acid catalysts, base catalysts, , nanocatalysts, etc. However, their use has several drawbacks, such as toxicity or the requirement of harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of α,β-Unsaturated Ketones in Water: The Claisen–Schmidt Condensation Revisited

Choudhury

Mahapatra

Sahu

et al. 2022

ACS Sustainable Chem. Eng.

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Carrying out organic synthesis in an aqueous medium is always challenging. Herein, we present a highly efficient method for the synthesis of α,β-unsaturated ketones in water through the Claisen−Schmidt condensation by using a green catalyst, choline hydroxide (ChOH). The products were isolated without any chromatographic separation technique. The catalyst shows high substrate tolerance and works well with electrondonating and electron-withdrawing substituted aromatic aldehydes. Not only is the catalyst metal-free and nontoxic, but it also offers the advantage of forming strong hydrogen bonds with the transition state and intermediates, facilitating the reaction and enhancing the product yield. A variety of substrate scopes has been explored. The catalysis happens at 50 °C in water which is the significant finding of this study. The reaction mechanism of this hydrogen-bond-mediated catalysis was thoroughly investigated with density functional theory (DFT). The plausible reaction pathway was proposed based on the energetics of the reactants, intermediates, transition states, and product. Further, quantum theory of atoms in molecules (QTAIM) and noncovalent interactions (NCI) index analyses were done to demonstrate the effects of strong hydrogen bonds in the crucial steps of the reaction pathway. The obtained results correlate well with our hypothesis and validate our proposed mechanism, suggesting that the hydrogen-bond-mediated catalysis needs special attention in carrying out organic synthesis in water.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of α,β-Unsaturated Ketones in Water: The Claisen–Schmidt Condensation Revisited

Choudhury

Mahapatra

Sahu

et al. 2022

ACS Sustainable Chem. Eng.

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“…Through the nucleophilic addition process, the intermediate d was formed with the help of the activated aldehyde molecule and enol form (Step 4). 40 Finally, by NJC Paper the elimination of the water molecule, the stable chalcone product was formed by the exclusion of the catalyst surface in step 5. The eliminated hierarchical MgO microsphere surface is again intricate as an effective catalyst surface to form the desired product in the reaction medium.…”

Section: Recyclability Leaching Study and Textural Properties Of The ...mentioning

confidence: 99%

Exploring the engineered hierarchical MgO microspheres as a selective catalyst for the Claisen–Schmidt condensation reaction

Bawiskar,

Srinivasappa,

Nikam

et al. 2024

New J. Chem.

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“…Regioselective condensation of 4-methyl-2-pentanone with 4chlorobenzaldehyde. [191] Patil et al [193] benzaldehyde Jain and Rani [101] Vanillin and acetone Yadav [161] Acetone with benzaldehyde Rano [83] Substituted benzalde- Winter et al [196] Benzaldehyde and aceto- Rajput and Kaur [198] Benzaldehyde and acetophenone Wagh and Yadav [204] protonation with protic acids and used in direct aldol reactions of 4-nitrobenzaldehyde with cyclohexanone. High yield was obtained for HBr as protonating acid due to a lower pKa value as the reaction was not inhibited by this acid.…”

Section: Organocatalysismentioning

confidence: 99%

Claisen‐Schmidt Condensation using Green Catalytic Processes: A Critical Review

Yadav

Wagh

2020

ChemistrySelect

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Claisen‐Schmidt condensation have historical significance for over140 years and the scope was expanded due to the realization that chalcones so synthesized possess biological activity. The principles of green chemistry with emphasis on use of different solid catalysts with proper distribution of active centers such as acid, base, acid‐base, organo‐ were used along with solvent‐less systems. Among solid bases layered double hydroxides (LDH)/hydrotalcites are the most common. The limitations of solid bases are overcome by solid acids and superacids. A number of metal oxide supports are used. MOFs are increasingly being used. Complex organo‐catalysts are employed for getting excellent regio‐selectivity. In certain metal oxides, both acidic and basic sites co‐exist on the pore surface of catalyst which offer superior results. Synergism of solid catalysis using microwaves and ultrasound to intensify rates and selectivity is in vogue.Controlled pore structure and distribution of active catalytic centers, whether mono‐, bi‐ or tri‐functional catalysts, will give better green and smart processes. The review gives a critical analysis of the area and presents future directions for research.

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Green synthesis of α-methylcinnamaldehyde via Claisen-Schmidt condensation of benzaldehyde with propanal over Mg–Zr mixed oxide supported on HMS

Cited by 12 publications

References 34 publications

Synthesis of α,β-Unsaturated Ketones in Water: The Claisen–Schmidt Condensation Revisited

Synthesis of α,β-Unsaturated Ketones in Water: The Claisen–Schmidt Condensation Revisited

Exploring the engineered hierarchical MgO microspheres as a selective catalyst for the Claisen–Schmidt condensation reaction

Claisen‐Schmidt Condensation using Green Catalytic Processes: A Critical Review

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