Journals / Turkish Journal of Chemistry / 2019 / Cilt: 43 - Sayı: 1

Preparation of α-hydroxyphenylacetic acid with cyclodextrins as an effective phase-transfer catalyst and its reaction mechanism

Pages
359–368
Publication Date
2022-11-05
DOI
—
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AI Summary & Key Takeaways

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⚡ TL;DR(Too Long; Didn't Read)

The results indicated that β -CD is the optimalcatalyst for the reported reaction (yield: 69.08%).

📌 3 Key Takeaways

🎯
Objective & Hypothesis:An effective procedure for the synthesis of α-hydroxyphenylacetic acid with cyclodextrin (CD) catalysts wasdeveloped.
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Key Findings & Data:The phase-transfer catalyst types, catalyst loadings, reaction times, reaction temperatures, and substratemolar ratios were investigated to optimize the reaction conditions.
💡
Conclusion & Impact:The results indicated that β -CD is the optimalcatalyst for the reported reaction (yield: 69.08%).
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

An effective procedure for the synthesis of α-hydroxyphenylacetic acid with cyclodextrin (CD) catalysts wasdeveloped. The phase-transfer catalyst types, catalyst loadings, reaction times, reaction temperatures, and substratemolar ratios were investigated to optimize the reaction conditions. In addition, the factors that affect the reaction werestudied, and the relationship between benzaldehyde and β -cyclodextrin (β -CD) was analyzed through 2D-ROESY. Theequilibrium constant when β -CD was used as the catalyst was calculated. The results indicated that β -CD is the optimalcatalyst for the reported reaction (yield: 69.08%). Furthermore, the mechanism underlying the reported reaction wasproposed.

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Cite This Article

ZHANG, R. X., HUANG, Q., WANG, Z. Z., CHU, H. M., TIAN, B. R. (2022). Preparation of α-hydroxyphenylacetic acid with cyclodextrins as an effective phase-transfer catalyst and its reaction mechanism. Turkish Journal of Chemistry, Cilt: 43 - Sayı: 1, 359–368. https://ajindex.com/articles/601666

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References (30)

  1. Lehn, J. M. J. Incl. Phenom. Macro. 1988, 6, 351-396
  2. Lehn, J. M. Rep. Prog. Phys. 2004, 67, 249-265
  3. Saenger, D. I. W. Angew. Chem. Int. Edit. 1980, 19, 344-362
  4. Ayala-Zavala, J. F.; Del-Toro-Sánchez, L.; Alvarez-Parrilla, E.; González-Aguilar, G. A. J. Food Sci. 2008, 73, 41-47
  5. Wang, Y.; Han, B. Chinese J. Chem. 2013, 31, 569-576
  6. Omari, M. M.; Badwan, A. A.; Zughul, M. B.; Eric, J.; Davies, D. Drug Dev. Ind. Pharm. 2007, 33, 1205-1215
  7. Szabó, Z. I.; Gál, R.; Gáll, Z.; Vancea, S.; Rédai, E.; Fülöp, I. J. Incl. Phenom. Macro. 2017, 88, 1-10
  8. Fineshamir, N.; Beig, A.; Zur, M.; Lindley, D.; Miller, J. M.; Dahan, A. Mol. Pharm. 2017, 14, 2138-2146
  9. Tamura, A.; Ohashi, M.; Yui, N. J. Biomat. Sci.-Polym. E. 2017, 28, 1124-1139
  10. Andersen, A. Int. J. Toxicol. 2006, 25, 11-27
  11. Dolphin, D. J. Heterocyclic Chem. 1970, 7, 275-283
  12. Abbas, K. A.; Khalil, S. K.; Shobirin, M. H. J. Agr. Sci. 2010, 2, 90-100
  13. Putten, P. L. V. Anton. Leeuw. Int. J. G. 1979, 45, 622-623
  14. Colon, D. F.; Pickard, S. T.; Smith, H. E. J. Org. Chem. 1991, 56, 2322-2326
  15. Resch, V.; Fabian, W. M.; Kroutil, W. Adv. Synth. Catal. 2010, 352, 993-997
  16. Damblon, C.; Jensen, M.; Ababou, A.; Barsukov, I.; Papamicael, C.; Schofield, C. J.; Olsen, L.; Bauer, R.; Roberts, G. C. J. Biol. Chem. 2003, 278, 29240-29251
  17. Bast, A.; Leurs, R.; Timmerman, H. Drugs 1987, 33, 67-74
  18. Yang, X.; Wang, X.; Liang, C.; Su, W.; Wang, C.; Feng, Z.; Li, C.; Qiu, J. Catal. Commun. 2008, 9, 2278-2281
  19. Sirimanne, S. R.; Patterson, D. G. J. Labelled Comp. Radiopharm. 1993, 33, 725-731
  20. Ayres, E. B.; Hauser, C. R. J. Am. Chem. Soc. 1943, 65, 1095-1096
  21. Chen, L.; Li, H.; Yu, F.; Wang, L. Chem. Commun. 2014, 50, 14866-14869
  22. Sowbna, P. R.; Yadav, G. D.; Ramkrishna, D. Aiche. J. 2012, 58, 3799-3809
  23. Yadav, G. D.; Sowbna, P. R. Chem. Eng. Res. Des. 2012, 90, 1281-1291
  24. Cheng-He, Z.; De-Qi, Y.; Ru-Gang, X. Synth. Commun. 1994, 24, 43-46
  25. Vilar, M.; Navarro, M. Electrochim. Acta 2011, 56, 305-313
  26. Djedaïni, F.; Lin, S. Z.; Perly, B.; Wouessidjewe, D. J. Pharm. Sci. 1990, 79, 643-646
  27. Misiuk, W.; Zalewska, M. Carbohyd. Polym. 2009, 77, 482-488
  28. Guo, Q. X.; Li, Z. Z.; Ren, T. A. N.; Zhu, X. Q.; Liu, Y. C. J. Incl. Phenom. Macrocycl. Chem. 1993, 17, 149-156
  29. Wimmer, R.; Aachmann, F. L.; Larsen, K. L.; Petersen, S. B. Carbohydr. Res. 2002, 337, 841-849
  30. Ferrazza, R.; Rossi, B.; Guella, G. J. Phys. Chem. B 2014, 118, 7147-7155. 31.