Solvent free synthesis of coumarin derivative by the use of AlSBA-1 molecular sieves

Mei Mei Peng; Pushparaj Hemalatha; Mani Ganesh; Muthiahpillai Palanichamy; Hyun Tae Jang

Journal of Industrial and Engineering Chemistry, Vol.20, No.3, 953-960, May, 2014

DOI10.1016/j.jiec.2013.06.028 Export Citation

Solvent free synthesis of coumarin derivative by the use of AlSBA-1 molecular sieves

Mei Mei Peng, Pushparaj Hemalatha, Mani Ganesh, Muthiahpillai Palanichamy, and Hyun Tae Jang^†

Department of Chemical Engineering, Hanseo University, Seosan-si 356 706, South Korea

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AlSBA-1 molecular sieves were synthesized successfully and used for the synthesis of coumarins through Pechmann condensation. The synthesized AlSBA-1 catalysts were characterized by XRD, BET, SEM, FTIR, TGA techniques. The synthesized materials possess large surface area with mesopores. Pechmann condensation of 3-methoxyphenol and ethyl acetoacetate was carried out under solvent free condition and 7-methoxy-4-methylcoumarin was the main product. The selectivity of the product was found to be 74.04%. Among the synthesized catalysts, AlSBA-1(2) showed high activity than others due to high density of acid sites. Hence, AlSBA-1 molecular sieves a better choice of catalyst for the synthesis of coumarins.

Keywords:AlSBA-1;Pechmann condensation;Coumarin derivative;3-Methoxyphenol;Ethyl acetoacetate

[References]

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Von Pechmann H, Duisberg C, Chem. Ber., 17, 929 (1884)
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Shriner RL, Org. React., 1, 1 (1942)
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Venkatachalam K, Palanichamy M, Murugesan V, Catal. Commun., 12, 299 (2010)
Vinu A, Murugesan V, Hartmann M, Chem. Mater., 15, 1385 (2003)
Balasubramanian VV, Anand C, Pal RR, Mori T, Bohlmann W, Ariga K, Tyagi AK, Vinu A, Microporous Mesoporous Mater., 121, 18 (2009)
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[Referenced By]

[1] O’Kennedy R, Thornes RD, Coumarins: Biology Applications and Mode of Action, first ed., John Wiley & Sons, Chichester, 1997. (1997)

[2] Constantinou AI, Kamath N, Hurley JS, Eur. J. Cancer, 34, 1927 (1998)

[3] Cooke D, Studies on the Mode of Action of Coumarins (Coumarin, 6-hydroxycoumarin, 7-hydroxycoumarin and Esculetin) at a Cellular Level, Dublin City University, Dublin, Ireland, 1999 (Ph.D. Thesis). (1999)

[4] Chen H, Walsh CT, Chem. Biol., 8, 301 (2001)

[5] Gutierrez-Sanchez C, Calvino-Casilda V, Perez-Mayoral E, Martin-Aranda RM, Lopez-Peinado AJ, Bejblova M, Cejka J, Catal. Lett., 128(3-4), 318 (2009)

[6] Zahradnik M, The Production, Application of Fluorescent Brightening Agents, John Wiley & Sons, New York, 1992. (1992)

[7] Murray RDH, Mendez J, Brown SA, The Natural Coumarins: Occurrence Chemistry and Biochemistry, John Wiley & Sons, New York, 1982. (1982)

[8] Von Pechmann H, Duisberg C, Chem. Ber., 17, 929 (1884)

[9] Johnson JR, Org. React., 1, 210 (1942)

[10] Jones G, Org. React., 15, 204 (1967)

[11] Shriner RL, Org. React., 1, 1 (1942)

[12] Narasimahan NS, Mali RS, Barve MV, Synthesis, 906 (1979)

[13] Woods LL, Sapp J, J. Org. Chem., 27, 3703 (1962)

[14] Bose DS, Rudradas AP, Babu MH, Tetrahedron Lett., 43, 9195 (2002)

[15] Sun P, Hu Z, Synth. Commun., 35, 1875 (2005)

[16] Shaabani A, Ghadari R, Rahmati A, Rezayan AH, J. Iran. Chem. Soc., 6, 710 (2009)

[17] Khaligh NG, Catal. Sci. Tech., 2, 1633 (2012)

[18] Li TS, Zhang ZH, Yang F, Fu CG, J. Chem. Res., 38 (1998)

[19] Gunnewegh EA, Hoefnagel AJ, Van Bekkum H, J. Mol. Catal. A-Chem., 100, 87 (1995)

[20] Hoefnagel AJ, Gunnewegh EA, Downing RS, Bekkum HV, J. Chem. Soc. Chem. Comm., 225 (1995)

[21] Sinhamahapatra A, Sutradhar N, Pahari S, Bajaj HC, Panda AB, Appl. Catal. A: Gen., 394(1-2), 93 (2011)

[22] Kalita P, Kumar R, Microporous Mesoporous Mater., 149, 1 (2012)

[23] Sudha S, Venkatachalam K, Priya SV, Mabel JH, Palanichamy M, Murugesan V, J. Mol. Catal. A-Chem., 291(1-2), 22 (2008)

[24] Venkatachalam K, Palanichamy M, Murugesan V, Catal. Commun., 12, 299 (2010)

[25] Vinu A, Murugesan V, Hartmann M, Chem. Mater., 15, 1385 (2003)

[26] Balasubramanian VV, Anand C, Pal RR, Mori T, Bohlmann W, Ariga K, Tyagi AK, Vinu A, Microporous Mesoporous Mater., 121, 18 (2009)

[27] Kao HM, Cheng CC, Mater. Lett., 60, 2594 (2006)

[28] Yadav GD, Ajgaonkar NP, Varma A, J. Catal., 292, 99 (2012)