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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 19
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Articles

A microwave-promoted atom-efficient diesterification of aromatic carboxylate with 1,4-dibromobutane in water

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Pages 2559-2565 | Received 26 Mar 2018, Published online: 12 Oct 2018

References

  • Badami, B. V. Concept of Green Chemistry: Redesigning Organic Synthesis. Reson. 2008, 13, 1041–1048. DOI:10.1007/s12045-008-0124-8.
  • Simon, M. O.; Li, C. J. Green Chemistry Oriented Organic Synthesis in Water. Chem. Soc. Rev. 2012, 41, 1415–1427. DOI:10.1039/C1CS15222J.
  • (a) Polishettiwar, V.; Varma, R. S. Aqueous Microwave Chemistry: A Clean and Green Synthetic Tool for Rapid Drug Discovery. Chem. Soc. Rev. 2008, 39, 1546–1557. DOI:10.1039/B716534J (b) Bai, L.; Wang, J. X. Reusable, Polymer‐Supported, Palladium‐Catalyzed, Atom‐Efficient Coupling Reaction of Aryl Halides with Sodium Tetraphenylborate in Water by Focused Microwave Irradiation. Adv. Synth. Catal. 2008, 350, 315–320. DOI:10.1002/adsc.200700361 (c) Bai, L. Atom-Efficient Coupling Reaction of Aryl Bromides with Sodium Tetraphenylborate Catalyzed by Reusable Pd/C in Water under Focused Microwave Irradiation. Chin. Chem. Lett. 2009, 20, 158–160. DOI:10.1016/j.cclet.2008.10.050.
  • Strauss, C. R.; Varma, R. S. Microwaves in Green and Sustainable Chemistry. Top. Curr. Chem. 2006, 266, 199–231. DOI:10.1007/128_060.
  • Haslam, E. Recent Developments in Methods for the Esterification and Protection of the Carboxyl Group. Tetrahedron 1980, 36, 2409–2433. DOI:10.1016/0040-4020(80)80219-5.
  • Ogliaruso, M. A.; Wolfe, J. F. The Synthesis of Carboxylic Acids and Esters and Their Derivatives; Wiley: Chichester, 1991. doi: 10.1002/9780470771587.ch7.
  • Parangi, T.; Wani, B.; Chudasama, U. Synthesis of Monoesters and Diesters Using Eco-Friendly Solid Acid Catalysts—Cerium(IV) and Thorium(IV) Phosphates. Appl. Catal. A- Gen. 2013, 467, 430–438. DOI:10.1016/j.apcata.2013.07.043.
  • Dakka, J.; Sasson, Y.; Khawaled, K.; Bram, G.; Loupy, A. Esterification of Carboxylic Acids by Benzyl Chloride Using Quaternary Ammonium Salts. J. Chem. Soc, Chem. Commun. 1991, 23, 853–854. DOI:10.1039/C39910000853.
  • Ooi, T.; Sugimoto, H.; Doda, K.; Maruoka, K. Esterification of Carboxylic Acids Catalyzed by in Situ Generated Tetraalkylammonium Fluorides. Tetrahedron Lett. 2001, 42, 9245–9248. DOI:10.1016/S0040-4039(01)02035-4.
  • Brinchi, L.; Germani, R.; Savelli, G. Ionic Liquids as Reaction Media for Esterification of Carboxylate Sodium Salts with Alkyl Halides. Tetrahedron Lett. 2003, 44, 2027–2029. DOI:10.1016/S0040-4039(03)00179-5.
  • Brinchi, L.; Germani, R.; Savelli, G. Efficient Esterification of Carboxylic Acids with Alkyl Halides Catalyzed by Fluoride Ions in Ionic Liquids. Tetrahedron Lett. 2003, 44, 6583–6585. DOI:10.1016/S0040-4039(03)01693-9.
  • Judeh, Z. M. A.; Shen, H. Y.; Chi, B. C.; Feng, L. C.; Selvasothi, S. A Facile and Efficient Nucleophilic Displacement Reaction at Room Temperature in Ionic Liquids. Tetrahedron Lett. 2002, 43, 9381–9384. DOI:10.1016/S0040-4039(02)02327-4.
  • Mcnulty, J.; Cheekoori, S.; Nair, J. J.; Larichev, V.; Capretta, A.; Robertson, A. J. A Mild Esterification Process in Phosphonium Salt Ionic Liquid. Tetrahedron Lett. 2005, 46, 3641–3644. DOI:10.1016/j.tetlet.2005.03.169.
  • Chinnappan, A.; Kim, H. Environmentally Benign Catalyst: Synthesis, Characterization, and Properties of Pyridinium Dicationic Molten Salts (Ionic Liquids) and Use of Application in Esterification. Chem. Eng. J. 2012, 187, 283–288. DOI:10.1016/j.cej.2012.01.101.
  • Likhanova, N.; Lijanova, I.; Morelos Alvarado, L.; Martinez Garcia, M.; Hernandez-Ortega, S.; Olivares Xometl, O. A New Route for the Synthesis of Methylene Dibenzoate by Using an Ionic Liquid. Coc. 2013, 17, 79–82. DOI:10.2174/138527213805289178v.
  • Jadhav, A. H.; Lee, K.; Koo, S.; Seo, J. G. Esterification of Carboxylic Acids with Alkyl Halides Using Imidazolium Based Dicationic Ionic Liquids Containing Bis-Trifluoromethane Sulfonimide Anions at Room Temperature. RSC Adv. 2015, 5, 26197–26208. DOI:10.1039/C5RA00802F.
  • Wessig, P.; Matthes, A. Preparation of Strained Axially Chiral (1, 5) Naphthalenophanes by Photo-dehydro-Diels − Alder Reaction. J. Am. Chem. Soc. 2011, 133, 2642–2650. DOI:10.1021/ja109118m.
  • Takahashi, M.; Ogiku, T.; Okamura, K.; Da, T. T.; Ohmizu, H.; Kondo, K.; Iwasaki, T. A New Synthesis of 2,2′-Disubstituted Unsymmetrical Biphenyls Based on the Intramolecular Ullmann Coupling Reaction Utilising Salicyl Alcohol as a Template. J. Chem. Soc. Perkin Trans. 1. 1993, 0, 1473–1479. DOI:10.1039/P19930001473.
  • Lewis, F. D.; Oxman, J. D.; Gibson, L. L.; Hampsch, H. L.; Quillen, S. L. Lewis Acid Catalysis of Photochemical Reactions. 4. Selective Isomerization of Cinnamic Esters. J. Am. Chem. Soc. 1986, 108, 3005–3015. DOI:10.1021/ja00271a033.
  • Sharghi, H.; Sarvari, M. H. Al2O3/MeSO3H (AMA) as a New Reagent with High Selective Ability for Monoesterification of Diols. Tetrahedron 2003, 59, 3627–3633. DOI:10.1016/S0040-4020(03)00518-0.
  • Shaw, J. E.; Kunerth, D. C. Quantitative Conversion of Carboxylic Acids and Phenols to Esters and Ethers by Reaction of Their Salts with Alkyl Halides. J. Org. Chem. 1974, 39, 1968–1970. DOI:10.1021/jo00927a048.
  • Holmberg, K.; Hansen, B. Methylene Diesters of Carboxylic Acids from Dichloromethane. Tetrahedron Lett. 1975, 16, 2303–2306. DOI:10.1016/S0040-4039(00)75108-2.
  • Caddick, S.; Mccarroll, A. J.; Sandham, D. A. A Convenient and Practical Method for the Selective Benzoylation of Primary Hydroxyl Groups Using Microwave Heating. Tetrahedron 2001, 57, 6305–6310. DOI:10.1016/S0040-4020(01)00592-0.
  • Ciuffreda, P.; Casati, S.; Santaniello, E. Lipase-Catalyzed Monoprotection of 1, 4-Diols in an Organic Solvent Using Vinyl Benzoate as Acyl Transfer Agent. Tetrahedron Lett. 2003, 44, 3663–3665. DOI:10.1016/S0040-4039(03)00694-4.
  • Ma, Y. H.; Wu, G.; Jiang, N.; Ge, S. W.; Zhou, Q.; Sun, B. W. Microwave-Assisted, Facile, Rapid and Solvent-Free One Pot Two-Component Synthesis of Some Special Acylals. Chin. Chem. Lett. 2015, 26, 81–84. DOI:10.1016/j.cclet.2014.11.001.
  • Bai, L.; Zhang, X. L.; Hu, W. H. The Reaction of p-Hdroxybenzoic Acid with Benzyl Chloride in Water. J. Gansu. Sci. 2008, 20, 82–85. DOI:10.16468/j.cnki.issn1004-0366.2008.02.019.

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