Green carbonyl condensation reactions demonstrating solvent and organocatalyst recyclability

Journal of Chemical Education

Volumn 90, Issue 8, 2013, Pages 1067-1070

  Stacey, Jason M ^a   Dicks, Andrew P ^a   Goodwin, Aaron A ^b   Rush, Brittney M ^b   Nigam, Manisha ^b  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Catalysis; Green Chemistry; Laboratory Instruction; Mechanisms of Reactions; Microscale Lab; NMR Spectroscopy; Organic Chemistry; Second Year Undergraduate; Solutions Solvents; Upper Division Undergraduate

Indexed keywords

EID: 84882283674     PISSN: 00219584     EISSN: 19381328     Source Type: Journal    
DOI: 10.1021/ed300819r     Document Type: Article

References (37)

1. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998; p 30.
2. Edward, A. R. Organic Waste Management and Recycling. In Green Organic Chemistry in Lecture and Laboratory; Dicks, A. P., Ed.; CRC Press: Boca Raton, FL, 2012; pp 199-224.
3. Weires, N. A.; Johnston, A.; Warner, D. L.; McCormick, M. M.; Hammond, K.; McDougal, O. M. Recycling of Waste Acetone by Fractional Distillation J. Chem. Educ. 2011, 88, 1724-1726
4. Wilkinson, T. J. Recycling Solvent Mixtures of Ethyl Acetate and Hexanes J. Chem. Educ. 1998, 75, 1640
5. Dussault, P. H.; Woller, K. R. Simple Procedures for Quantification and Reuse of Common Organic Solvent Mixtures Chem. Educ. 1996, 1, 1-6
6. Andraos, J.; Dicks, A. P. Green Chemistry Teaching in Higher Education: A Review of Effective Practices Chem. Educ. Res. Pract. 2012, 13, 69-79
7. Mak, K. K. W.; Siu, J.; Lai, Y. M.; Chan, P.-k. Mannich Reactions in Room Temperature Ionic Liquids (RTILs): An Advanced Undergraduate Project of Green Chemistry and Structural Elucidation J. Chem. Educ. 2006, 83, 943-946
8. Forsyth, S. A.; Gunaratne, H. Q. N.; Hardacre, C.; McKeown, A.; Rooney, D. W. One-Pot Multistep Synthetic Strategies for the Production of Fenpropimorph Using an Ionic Liquid Solvent Org. Process Res. Dev. 2005, 10, 94-102
9. Young, D. M.; Welker, J. J. C.; Doxsee, K. M. Green Synthesis of a Fluorescent Natural Product J. Chem. Educ. 2011, 88, 319-321
10. Novak, M.; Wang, Y.-T.; Ambrogio, M. W.; Chan, C. A.; Davis, H. E.; Goodwin, K. S.; Hadley, M. A.; Hall, C. M.; Herrick, A. M.; Ivanov, A. S.; Mueller, C. M.; Oh, J. J.; Soukup, R. J.; Sullivan, T. J.; Todd, A. M. A Research Project in the Organic Instructional Laboratory Involving the Suzuki-Miyaura Cross Coupling Reaction Chem. Educ. 2007, 12, 414-418
11. Miles, W. H.; Connell, K. B. Synthesis of Methyl Diantilis, a Commercially Important Fragrance J. Chem. Educ. 2006, 83, 285-286
12. Doyle, M. P.; Plummer, B. F. Replacing Mineral Acids in the Laboratory: Nafion-Catalyzed Dehydration and Esterification J. Chem. Educ. 1993, 70, 493-495
13. Viswanathan, T.; Jethmalani, J. The Aqueous Ring-Opening Metathesis Polymerization of Furan-Maleic Anhydride Adduct: Increased Catalytic Activity Using a Recyclable Transition Metal Catalyst J. Chem. Educ. 1993, 70, 165-167
14. Reed, S. M.; Hutchison, J. E. Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid J. Chem. Educ. 2000, 77, 1627-1629
15. Chen, J.; Spear, S. K.; Huddleston, J. G.; Rogers, R. D. Polyethylene Glycol and Solutions of Polyethylene Glycol as Green Reaction Media Green Chem. 2005, 7, 64-82
16. Gu, Y. Multicomponent Reactions in Unconventional Solvents: State of the Art Green Chem. 2012, 14, 2091-2128
17. McKenzie, L. C.; Huffman, L. M.; Hutchison, J. E.; Rogers, C. E.; Goodwin, T. E.; Spessard, G. O. Greener Solutions for the Organic Chemistry Teaching Lab: Exploring the Advantages of Alternative Reaction Media J. Chem. Educ. 2009, 86, 488-493
18. Yadav, G. D.; Motirale, B. G. Microwave-Irradiated Synthesis of Nitrophen Using PEG-400 as Phase Transfer Catalyst and Solvent Org. Process Res. Dev. 2009, 13, 341-348
19. Wade, E. O.; Walsh, K. E. A Multistep Organocatalysis Experiment for the Undergraduate Organic Laboratory: An Enantioselective Aldol Reaction Catalyzed by Methyl Prolinamide J. Chem. Educ. 2011, 88, 1152-1154
20. Wong, T. C.; Sultana, C. M.; Vosburg, D. A. A Green, Enantioselective Synthesis of Warfarin for the Undergraduate Organic Laboratory J. Chem. Educ. 2010, 87, 194-195
21. Bennett, G. D. A Green Enantioselective Aldol Condensation for the Undergraduate Organic Laboratory J. Chem. Educ. 2006, 83, 1871-1872
22. Lazarski, K. E.; Rich, A. A.; Mascarenhas, C. M. A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory J. Chem. Educ. 2008, 85, 1531-1534
23. Raston, C. L.; Cave, G. W. V. Green Chemistry Laboratory: Benign Synthesis of 4,6-Diphenyl[2,2′]bipyridine via Sequential Solventless Aldol and Michael Addition Reactions J. Chem. Educ. 2005, 82, 468-469
24. Wachter-Jurcsak, N.; Reddin, K. Discovery-Oriented Approach to Organic Synthesis: Tandem Aldol Condensation-Michael Addition Reactions. Identifying Diastereotopic Hydrogens in an Achiral Molecule by NMR Spectroscopy J. Chem. Educ. 2001, 78, 1264-1265
25. Clausen, T. P.; Johnson, B.; Wood, J. A Mixed Aldol Condensation-Michael Addition Experiment J. Chem. Educ. 1996, 73, 266
26. Coutlangus, M. L.; Filla, S. A.; Rowland, A. T. A Tandem Michael-Aldol Reaction Sequence: An Undergraduate Research Organic Experiment J. Chem. Educ. 1989, 66, 520-522
27. Garcia-Raso, A.; Garcia-Raso, J.; Sinisterra, J. V.; Mestres, R. Michael Addition and Aldol Condensation: A Simple Teaching Model for Organic Laboratory J. Chem. Educ. 1986, 63, 443
28. Kumar, D.; Patel, G.; Mishra, B. G.; Varma, R. S. Eco-Friendly Polyethylene Glycol Promoted Michael Addition Reactions of α,β- Unsaturated Carbonyl Compounds Tetrahedron Lett. 2008, 49, 6974-6976
29. Liu, Y.; Liang, J.; Liu, X. H.; Fan, J. C.; Shang, Z. C. Polyethylene Glycol (PEG) as a Benign Solvent for Knoevenagel Condensation Chin. Chem. Lett. 2008, 19, 1043-1046
30. Firouzeh, N.; Hossein, K. A Green and Highly Efficient Protocol for Catalyst-free Knoevenagel Condensation and Michael Addition of Aromatic Aldehydes with 1,3-Cyclic Diketones in PEG-400 Chin. J. Chem. 2011, 29, 2407-2410
31. Abhyankar, S. B. Introduction to Teaching Green Organic Chemistry. In Green Organic Chemistry in Lecture and Laboratory; Dicks, A. P., Ed.; CRC Press: Boca Raton, FL, 2012; pp 6-13.
32. List, B. Proline-Catalyzed Asymmetric Reactions Tetrahedron 2002, 58, 5573-5590
33. Bermúdez, E.; Ventura, O. N.; Saenz Méndez, P. Mechanism of the Organocatalyzed Decarboxylative Knoevenagel-Doebner Reaction. A Theoretical Study J. Phys. Chem. A 2010, 114, 13086-13092
34. Stabile, R. G.; Dicks, A. P. Two-Step Semi-Microscale Preparation of a Cinnamate Ester Sunscreen Analog J. Chem. Educ. 2004, 81, 1488-1491
35. Kolb, K. E.; Field, K. W.; Schatz, P. F. A One-Step Synthesis of Cinnamic Acids Using Malonic Acid: The Verley-Doebner Modification of the Knoevenagel Condensation J. Chem. Educ. 1990, 67, A304
36. Crouch, R. D.; Holden, M. S. An Organic Puzzle Using Meldrum's Acid J. Chem. Educ. 2002, 79, 477-478
37. Minea, L. M.; Dicks, A. P. A Coumarin Mystery-The Case of the Missing Methyl Groups Chem. Educ. 2009, 14, 105-107