Asian Journal of Research in Chemistry

Open Access Open Access  Restricted Access Subscription Access
Open Access Open Access Open Access  Restricted Access Restricted Access Subscription Access

An optimized method for synthesis of 2’hydroxy chalcone


Affiliations
1 Research Scholar, Department of Pharmaceutical Chemistry, A.R College of Pharmacy and G.H Patel Institute of Pharmacy, Vallabh Vidhyanagar, Anand, Gujarat, India, India
2 Professor, Department of Pharmaceutical Chemistry, A.R College of Pharmacy and G.H Patel Institute of Pharmacy, Vallabh Vidhyanagar, Anand, Gujarat, India., India
     

   Subscribe/Renew Journal


The main aim of present work is to develop optimised method for synthesis of 2’hydroxy chalcone. 2’hydroxy chalcone was synthesized by Claisen–Schmidt condensation between o-hydroxy acetohenone and benzaldehyde. Variety of bases tried as catalyst for synthesis of 2’hydroxy chalcone. Calcium hydroxide and magnesium hydroxide proved ineffective for synthesis. Lithium hydroxide slightly converts reactant to product. Sodium hydroxide shows best catalytical activity compare to other bases. Isopropyl alcohol proved better solvent then other solvents like methanol, ethanol, acetonitrile, dichloromethane and tetrahydrofuran. In optimization step, effect of solvent and base quantity, stirring time and temperature was examined. Temperature shows drastic effect on product yield and purity. At 0˚C best yield was obtained. Amount of base catalyst also shows significant effect on yield. 20ml of 40% NaOH gives best results for 0.05mol reactants. 50ml IPA was needed for the best results for 0.05mol reactant. In approximate 4h, reaction should be completed. Further stirring was not too much effective.

Keywords

2’ hydroxyl chalcone, Claisen–Schmidt condensation, IPA, NaOH
Subscription Login to verify subscription
User
Notifications
Font Size


  • Shima H. M. E. Ketabforoosh et al. Synthesis and Anti-Cancer Activity Evaluation of New Dimethoxylated Chalcone and Flavanone Analogs. Arch. Pharm. Chem. Life Sci. 2014; 347: 1–8.

  • Bhagyesh Baviskar, Sureshbhi Patel, Bhushan Baviskar, SS Khadabadi, Mahendra Shiradkar. Design and Synthesis of Some Novel Chalcones as Potent Antimicrobial Agent. Asian J.Research Chem. 2008; 1(2): 67-69.

  • Bhaskar S. Dawane, Baseer M Shaikh, Namdev T. Khandare, Gajanan G. Mandawad, Santosh S. Chobe, Shankaraiah G. Konda. Synthesis of Some Novel Substituted Pyrazole Based Chalcones and Their In-Vitro Antimicrobial Activity. Asian J. Research Chem. 2010; 3(1): 90-93.

  • H.V. Shahare, G.R. Pawar, S.S. Patil, P.D. Patil. Synthesis and Biological Evaluation of New Chalcone Analogs. Asian J.Research Chem. 2011; 4(2): 237-240.

  • Gopi C., Dhanaraju M. D. Synthesis, Characterization and AntiMicrobial Evaluation of Derivative of Chalcone. Asian J. Research Chem. 2011; 4(2): 181-182.

  • Gondu Eswara Rao, S.A. Rahaman, A. Prameela Rani, Ch. M.M. Prasada Rao. Synthesis, Characterization and Antimicrobial Activity of Novel Chalcones from 1-[4-(1H-imidazol-1-yl) Phenyl] Ethanone. Asian J. Research Chem. 2013; 6(7): 687-689.

  • Pushkar Pratap Singh, B. Jayalakshmi, N. Senthil Kumar. Synthesis, Characterization and Antimicrobial Evaluation of Some New Chalcones. Asian J. Research Chem. 2013; 6(12): 1133-1136.

  • Suha K. Al-Mosawi, Hanan A. Al-Hazam, Abbas F. Abbas.Synthesis, Characterization and Biological Study of Some Chalcones derived from Terphthaldehyde. Asian J. of Research Chem. 2019; 12(3): 153-156. DOI: 10.5958/09744150.2019.00031.2

  • M. Safavi et al. Halogenated flavanones as potential apoptosisinducing agents: Synthesis and biological activity evaluation. European Journal of Medicinal Chemistry. 2012; 58: 573-580.

  • Y. Murti and P. Mishra. Synthesis and Evaluation of Flavanones as Anticancer Agents. Indian Journal of Pharmaceutical Sciences.2014; 76(2): 163-166.

  • Yeonjoong Y, Hwang SA and Yoon H. 1H and 13C NMR spectral assignments of 2-hydroxychalcones. Magn. Reson. Chem. 2013; 51: 364–370.

  • Cabrera M., Simoens M., Falchi G. and Lavaggi M.L. Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure activity relationships.Bioorganic and Medicinal Chemistry. 2007; 15: 3356–3367.

  • Laxmi Lal Dangi, Mangal S. Dulawat, Parul Tiwari, Shiv Singh Dulawat. New substituted m-Phenoxy chalcones; their synthesis by microwave irradiation and antifungal activity. Asian J.Research Chem. 2013; 6(5): 461-463.

  • Albogami A.S., Karama U., Amousa A.A, Khan M., Al-mazroa S.A and Alkhathlan A.Z. Simple and Efficient One Step Synthesis of Functionalized Flavanones and Chalcones. Orient. J. Chem.

  • ; 28(2): 619-626.

  • Sharma N and Joshi YC. Synthesis of substituted chalcones under solvent–free microwave irradiation conditions and their antimicrobial evaluation. International Journal of Pharmacy and Pharmaceutical Sciences. 2012; 4(4): 436-439.

  • Borse SL. PhD. Thesis. Microwave Assisted Synthesis of Substituted Flavonoids and Pharmacological Evaluation.” Shri Jagdish Prasad Jhabarmal Tibrewala University, 2010.

  • Thornton M.T. PhD. Thesis. Synthesis of flavonoids and flavonoid-based designed multiple ligands for hypertension. Deakin University January, 2013, 32-33.

  • K. Ishwar Bhat, Ranee Kumari, Abhishek Kumar, Pankaj Kumar.Synthesis of Some Novel Flavanones and Evaluation of Antioxidant Activities. Research J. Pharm. and Tech. 2019; 12(5): 2141-2144 DOI: 10.5958/0974-360X.2019.00355.X

  • Pramod Kulkarni, Pradip Wagh and Pudukulathan Zubaidha. An Improved and Eco-Friendly Method for the Synthesis of Flavanone by the Cyclization of 2’-Hydroxy Chalcone using Methane Sulphonic Acid as Catalyst. Chemistry Journal. 2012; 2(3): 106-110.

  • Preet Anand and Baldev Singh. Synthesis and evaluation of novel carbamate-substituted flavanone derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents. Med Chem Res. 2013; 22: 1648–1659. doi 10.1007/s00044-012-0162-3.

  • Yuh-Meei Lin, Yasheen Zhou, Michael T. Flavin, Li-Ming Zhou, Weiguo Niea and Ching Chen. Chalcones and Flavonoids as AntiTuberculosis Agents”, Bioorganic & Medicinal Chemistry. 2002; 10: 2795–2802.

  • Yogesh Murti and Pradeep Mishra. Flavanone: A Versatile Heterocyclic Nucleus. International Journal of ChemTech Research. 2014; 6(5): 3160-3178.

  • Srinivasu V. N. Vuppalapati, Likai Xia, Naushad Edayadulla, Yong Rok Lee. Mild and Efficient One-Pot Synthesis of Diverse Flavanone Derivatives via an Organocatalyzed Mannich-Type Reaction. Synthesis. 2014; 46: 465–474.

  • Moorthy N.S.H.N, Singh R.J, Singh H.P, and Gupta S.D. Synthesis, Biological Evaluation and In Silico Metabolic and Toxicity Prediction of Some Flavanone Derivatives. Chem. Pharm. Bull. 2006; 54(10): 1384-1390.

  • S. Saravanamurugan, M. Palanichamy, Banumathi Arabindoo, V. Murugesan. Solvent free synthesis of chalcone and flavanone over zinc oxide supported metal oxide catalysts. Catalysis Communications. 2005; 6: 399-403.

  • Elzbieta Budzisz et al. Biological Evaluation of 3- Benzylidenechromanones and Their Spiropyrazolines-Based Analogues. Molecules. 2020; 25: 1613.

  • Lincy Joseph, Mathew George. Analgesic and Anti-Oxidant Activities of Certain (E)-3 Arylidene Flavanones Synthesized by One Pot Method. Asian Journal of Research in Chemistry. 2009;

  • (3): 318-321.


Abstract Views: 139

PDF Views: 0




  • An optimized method for synthesis of 2’hydroxy chalcone

Abstract Views: 139  |  PDF Views: 0

Authors

Nikunj Patadiya
Research Scholar, Department of Pharmaceutical Chemistry, A.R College of Pharmacy and G.H Patel Institute of Pharmacy, Vallabh Vidhyanagar, Anand, Gujarat, India, India
Vipul Vaghela
Professor, Department of Pharmaceutical Chemistry, A.R College of Pharmacy and G.H Patel Institute of Pharmacy, Vallabh Vidhyanagar, Anand, Gujarat, India., India

Abstract


The main aim of present work is to develop optimised method for synthesis of 2’hydroxy chalcone. 2’hydroxy chalcone was synthesized by Claisen–Schmidt condensation between o-hydroxy acetohenone and benzaldehyde. Variety of bases tried as catalyst for synthesis of 2’hydroxy chalcone. Calcium hydroxide and magnesium hydroxide proved ineffective for synthesis. Lithium hydroxide slightly converts reactant to product. Sodium hydroxide shows best catalytical activity compare to other bases. Isopropyl alcohol proved better solvent then other solvents like methanol, ethanol, acetonitrile, dichloromethane and tetrahydrofuran. In optimization step, effect of solvent and base quantity, stirring time and temperature was examined. Temperature shows drastic effect on product yield and purity. At 0˚C best yield was obtained. Amount of base catalyst also shows significant effect on yield. 20ml of 40% NaOH gives best results for 0.05mol reactants. 50ml IPA was needed for the best results for 0.05mol reactant. In approximate 4h, reaction should be completed. Further stirring was not too much effective.

Keywords


2’ hydroxyl chalcone, Claisen–Schmidt condensation, IPA, NaOH

References