AMMONIUM CHLORIDE CATALYZED ALDOL CONDENSATION: A FACILE SYNTHESIS OFα, α’- BIS (SUBSTITUTED BENZYLIDENE) CYCLOALKANONES

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TEIMOURI F.; HADI KHEZRI S.; MIRI Z.; EFTEKHARI SIS B.; AZIZIAN J.

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Journal: JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY) Year:2009 | Volume:19 | Issue:72 (CHEMISTRY ISSUE) Page(s): 103-108

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Title

AMMONIUM CHLORIDE CATALYZED ALDOL CONDENSATION: A FACILE SYNTHESIS OFα, α’- BIS (SUBSTITUTED BENZYLIDENE) CYCLOALKANONES

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Keywords

αQ3

α'-BIS(SUBSTITUTED BENZYLIDENE)KETONESQ3

CROSS ALDOL CONDENSATIONQ3

AMMONIUM CHLORIDEQ3

Abstract

Introduction: Aldol condensation is a powerful tool for the formation of carboncarbon bond in many classes of carbonyl compounds. This reaction is performed in the presence of acids, bases or different complexes of metal (II) ions as catalyst. According to importance of this reaction, efforts were done to achieve an efficient catalyst in order to improve aldol condensation.Aims: The catalytic effect of AMMONIUM CHLORIDE was determined in CROSS ALDOL CONDENSATION to afford the corresponding a, a' -bis (substituted benzylidene) cycloalkanones also, AMMONIUM CHLORIDE with previously reported catalysts was compared in this reaction.Materials and Methods: Aldol condensation of cyclopentanone and benzaldehyde in ethanol was selected as model reaction. In the absence of AMMONIUM CHLORIDE no product was obtained either at room temperature or at reflux condition. Increasing the amount of catalyst, improve the yield of reaction (room temperature). Raising the temperature of the reaction (reflux condition) caused little amount of catalyst gave higher yields. Based on the experiments with the optimized condition, aldol condensation of cyclopentanone and cyclohexanone with aromatic aldehyde with electron donating and withdrawing groups was done.Results: AMMONIUM CHLORIDE efficiently catalyzes CROSS ALDOL CONDENSATION of aromatic aldehydes with ketones to afford the corresponding a, a' -bis (substituted benzylidene) cycloalkanones in high yields. NH4Cl compared with previously reported catalysts reflects the wide applicability and usefulness of the method.Conclusion: NH4Cl is an efficient and readily available reagent and inexpensive catalyst in CROSS ALDOL CONDENSATIONs of different ketones with various aromatic aldehydes to prepare the a, a' -bis (substituted benzylidene) cycloalkanones. The reaction is a green process avoiding the use of toxic solvents and acid liquids.

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APA: Copy

TEIMOURI, F., HADI KHEZRI, S., MIRI, Z., EFTEKHARI SIS, B., & AZIZIAN, J.. (2009). AMMONIUM CHLORIDE CATALYZED ALDOL CONDENSATION: A FACILE SYNTHESIS OFα, α’- BIS (SUBSTITUTED BENZYLIDENE) CYCLOALKANONES. JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY), 19(72 (CHEMISTRY ISSUE)), 103-108. SID. https://sid.ir/paper/70617/en

Vancouver: Copy

TEIMOURI F., HADI KHEZRI S., MIRI Z., EFTEKHARI SIS B., AZIZIAN J.. AMMONIUM CHLORIDE CATALYZED ALDOL CONDENSATION: A FACILE SYNTHESIS OFα, α’- BIS (SUBSTITUTED BENZYLIDENE) CYCLOALKANONES. JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY)[Internet]. 2009;19(72 (CHEMISTRY ISSUE)):103-108. Available from: https://sid.ir/paper/70617/en

IEEE: Copy

F. TEIMOURI, S. HADI KHEZRI, Z. MIRI, B. EFTEKHARI SIS, and J. AZIZIAN, “AMMONIUM CHLORIDE CATALYZED ALDOL CONDENSATION: A FACILE SYNTHESIS OFα, α’- BIS (SUBSTITUTED BENZYLIDENE) CYCLOALKANONES,” JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY), vol. 19, no. 72 (CHEMISTRY ISSUE), pp. 103–108, 2009, [Online]. Available: https://sid.ir/paper/70617/en

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