Microwave-Assisted Organic Reactions: Eco-friendly Synthesis of Dibenzylidenecyclohexanone Derivatives via Crossed Aldol Condensation


Sri Handayani(1*), Cornelia Budimarwanti(2), Winarto Haryadi(3),

(1) Chemistry Education Department, Faculty of Mathematics and Natural Science, Yogyakarta State University
(2) Chemistry Education Department, Faculty of Mathematics and Natural Science, Yogyakarta State University
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada
(*) Corresponding Author


The synthesis of dibenzylidenecyclohexanone derivatives via environmentally friendly Microwave Assisted Organic Synthesis (MAOS) crossed aldol condensation had been carried out. The condensation reaction to synthesize the dibenzylidenecyclohexanone 8b was performed by reacting benzaldehyde 4 and cyclohexanone 2 (mole ratio of 2:1) with NaOH as catalyst for 2 min under microwave irradiation. The benzaldehyde derivatives used in this study were 4-methoxybenzaldehyde and 3,4-dimethoxybenzaldehyde and gave of (2E,6E)-bis(4-methoxy benzylidene)cyclohexanone 8a and (2E,6E)-bis(3,4-dimethoxybenzylidene)cyclohexanone 8c, respectively. The study was commenced by searching the optimum concentration of NaOH. The reaction yield was determined by TLC scanner and the structure was elucidated by FTIR and NMR spectrometers. For the comparison, the reaction was also carried out by using stirring method. The results showed that optimum concentration of NaOH was 5 mmole. By using the optimum condition via MAOS method, the compounds 8a, 8b and 8c were obtained in 100, 98 and 93%, respectively. The research also proved that the method of dibenzylidenecyclohexanones (8) synthesis using MAOS was more efficient than stirring method.


dibenzylidenecyclohexanone; MAOS; eco-friendly

Full Text:

Full Text PDF


[1] Sardjiman, 2000, Synthesis of some new series of curcumin analogues, antioxidative, antiinflamatory, antibacterial activities and qualitative-structure activity relationship, Dissertation, Universitas Gadjah Mada.

[2] Handayani, S., and Arty, I.S., 2008, Synthesis of hydroxyl radical scavengers from benzalacetone and its derivatives, J. Phys. Sci., 19 (2), 61–68.

[3] Yamagami, C., Akamatsu, M., Motohashi, N., Hamada, S., and Tanahashi, T., 2005, Quantitative structure-activity relationship studies for antioxidant hydroxybenzalacetones by quantum chemical- and 3-D-QSAR(CoMFA) analyses, Bioorg. Med. Chem. Lett., 15 (11), 2845–2850.

[4] Handayani, S., 2012, Synthesis of benzalacetone analogue over NaOH-/ZrO2-montmorillonite as catalyst and its antioxidant activity test, Dissertation, Universitas Gadjah Mada.

[5] Motohashi, N., Ashihara, Y., Yamagami, C., and Saito, Y., 2001, Structure–antimutagenic activity relationships of benzalacetone derivatives against UV-induced mutagenesis in E. coli WP2uvrA and γ-induced mutagenesis in Salmonella typhimurium TA2638, Mutat. Res.-Fund. Mol. Mech. Mutagen., 474 (1-2), 113–120.

[6] Napoleon, A.A., Khan, F.R.N., Jeong, E.D., and Chung, E.H.,, 2015, Potential anti-tubercular agents : Hexahydro-3-phenyl indazol-2-yl(pyridin-4-yl)methanones from anti-tubercular drug isoniazid and bis(substituted-benzylidene)cyclo alkanones, Chin. Chem. Lett., 26 (5), 567–571.

[7] Da’i, M., Supardjan, A.M., Meiyanto, E., and  Jenie, U.A., 2007, Isomers geometric dan efek sitotoksik pada sel T47D dari analog kurkumin PGV-0 and PGV-1, Indonesian J. Pharm., 18 (1), 40–47.

[8] Buck, J.R., Saleh, S., Uddin, M.I., and Manning, H.C., 2012, Rapid, microwave-assisted organic synthesis of selective V600EBRAF inhibitors for preclinical cancer research, Tetrahedron Lett., 53 (32), 4161–4165.

[9] Guofeng, C., Jitai, L., Huiyun, D., and Tongshuang, L., 2004, Improved ultrasound-induced synthesis of 1,5-diaryl-1,4-pentadien-3-ones, CJI, 6 (1), 7.

[10] Lutic, D., 2010, Heterogeneous acid-base catalyzed aldol condensation : Acetaldehyde and heptaldehyde on hydrotalcites. Optimization of operatory conditions, Acta Chem. IASI, 46, 31–46.

[11] Ebitani, K., Motokura, K., Mori, K., Mizugaki, T., Kaneda, K., and Hart, C., 2006, Reconstructed hydrotalcite as a highly active heterogeneous base catalyst for carbon-carbon bond formations in the presence of water, J. Org. Chem., 71 (15), 5440–5447.

[12] Handayani, S., Matsjeh, S., Anwar, C., Atun, S., and Fatimah, I., 2012, Reaction efficiency of crossed-aldol condensation between acetone and benzaldehyde over ZrO2 and ZrO2-montmorillonite catalyst, J. Appl. Sci. Res., 8 (5), 2457–2464.

[13] Handayani, S., Matsjeh, S., Anwar, C., Atun, S., and Fatimah, I., 2012, Novel synthesis of 1,5-dibenzalacetone using NaOH/ZrO2-montmorillonite as cooperative catalyst, Int. J. Chem. Anal. Sci., 3 (6), 6–10.

[14] Pudjono, Sismindari, and Widada, H., 2008, Synthesis of 2,5-bis-(4’-hydroxybenzylidene)cyclo pentanone and 2,5-bis(4’-chlorobenzylidene)cyclo pentanone compounds and antiproliferative test to HeLa cells, Indonesian J. Pharm., 19 (1), 48–55.

[15] Handayani, S., Arianingrum, R., and Haryadi, W., 2011, Vanillin structure modification of isolated vanilla fruit (Vanilla planifolia Andrews) to form vanillinacetone, 14th Asian Chemical Conggres, Bangkok, 5-8 September 2011, 252–258.

[16] Salehi, P., Khodaei, M.M., Zolfigol, M.A., and Keyvan, A., 2002, Solvent-free crossed aldol condensation of ketones with aromatic aldehydes mediated by magnesium hydrogensulfate, Monatsh.Chem., 133 (10), 1291–1295.

[17] Sheldon, R.A., Arends, I., and Hanefeld, U., 2007, Green Chemistry and Catalysis. Weinheim: Wiley-VCH.

[18] Lin, J.S., Chung, M.H., Chen, C.M., Juang, F.S., and Liu, L.C., 2011, Microwave-assisted synthesis of organic/inorganic hybrid nanocomposites and their encapsulating applications for photoelectric devices, J. Phys. Org. Chem., 24 (3), 193–202.

[19] Rebrov, E.V., 2012, Microwave-assisted organic synthesis in microstructured reactors, Russ. J. Gen. Chem., 82 (12), 2060–2069.

[20] Martin, E., and Kellen-Yuen, C., 2007, Microwave-assisted organic synthesis in the organic teaching lab: A simple, greener Wittig reaction, J. Chem. Educ., 84 (12), 2004–2006.

[21] Pavia, D.L., Lampman, G.M., Kriz, G.S., and Vyvyan, J.A., 2009, Introduction to Spectroscopy, 4th Ed., Washington: Brooks/Cole.

[22] Wang, C., Liu, J., Leng, W., and Gao, Y., 2014, Rapid and efficient functionalized ionic liquid-catalyzed aldol condensation reactions associated with microwave irradiation, Int. J. Mol. Sci., 15 (1), 284–1299.

[23] Jain, A.K., and Singla, R.K., 2011, An overview of microwave assisted technique: Green synthesis, Webmedcentral Pharm. Sci., 2 (9), 1–18.

[24] Kuhnert, N., 2002, Microwave-assisted reactions in organic synthesis-are there any nonthermal microwave effects?, Angew. Chem. Int. Ed., 41 (11), 1863–1866.

[25] Lidström, P., Tierney, J., Wathey, B., and Westman, J., 2001, Microwave assisted organic synthesis-A review, Tetrahedron, 57 (45), 9225–9283.

[26] Moseley, J.D., and Kappe, C.O., 2011, A critical assessment of the greenness and energy efficiency of microwave-assisted organic synthesis, Green Chem., 13 (4), 794–806.

DOI: https://doi.org/10.22146/ijc.25460

Article Metrics

Abstract views : 34 | views : 64


  • There are currently no refbacks.

Copyright (c) 2017 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Indexed by:

Creative Commons License
Indonesian Journal of Chemistry is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.


View The Statistics of Indones. J. Chem.