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Efficient Synthesis of p-Hydroxyphenyl Ethanol from Hydrogenation of Methyl p-Hydroxyphenylacetate with CNTs-promoted Cu-Zr Catalyst

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Abstract

Hydrogenation of methyl p-hydroxyphenylacetate has been used for the synthesis of p-hydroxyphenyl ethanol. The reaction was catalyzed by CuiZrj-x%(mass fraction) carbon nanotubes(CNTs) catalysts. Incorporation of a minor amount of CNTs into CuiZrj oxide can visibly increase the catalytic activity for the synthesis of p-hydroxyphenyl ethanol. The yield of p-hydroxyphenyl ethanol reaches 94.2% over a co-precipitated catalyst of Cu3Zr1 oxide with 11.0%CNTs. Its catalytic activity shows no obvious decrease after three cycles. This is much better than the CNT-free co-precipitated catalyst with a good yield of 81.1%, Cu3Zr1-0%CNTs.

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References

  1. Brown H. C., Narasimhan S., Choi Y. M., J. Org. Chem., 1982, 47, 4702

    Article  CAS  Google Scholar 

  2. Chen P., Zhang H. B., Lin G. D., Hong Q., Tsai K. R., Carbon, 1997, 35, 1495

    Article  CAS  Google Scholar 

  3. Zhou Q., Reekie T. A., Abbassi R. H., Indurthi V. D., Font J. S., Ryan R. M., Munoz L., Kassiou M., Bioorg. Med. Chem., 2018, 26, 5852

    Article  CAS  Google Scholar 

  4. Venkateswarlu S., Panchagnula G. K., Subbaraju G. V., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 2006, 45B, 1063

    CAS  Google Scholar 

  5. Baraldi P. G., Cacciari B., Romagnoli R., Spalluto G., Monopoli A., Ongini E., Varani K., Borea P. A., J. Med. Chem., 2002, 45, 115

    Article  CAS  Google Scholar 

  6. Mellor S. B., Nielsen A. Z., Burow M., Motawia M. S., Jakubauskas D., Moeller B. L., Jensen P. E., ACS Chem. Biol., 2016, 11, 1862

    Article  CAS  Google Scholar 

  7. Xie J., Yang F., Zhang M., Lam C., Qiao Y., Xiao J., Zhang D., Ge Y., Fu L., Xie D., Bioorg. Med. Chem. Lett., 2017, 27, 131

    Article  CAS  Google Scholar 

  8. Alvarez Calero J. M., Jorge Z. D., Massanet G. M., Org. Lett., 2016, 18, 6344

    Article  CAS  Google Scholar 

  9. Brenna E., Fronza G., Fuganti C., Pinciroli M., Journal of Agricultural and Food Chemistry, 2003, 51, 4866

    Article  CAS  Google Scholar 

  10. Pinedo-Rivilla C., Aleu J., Collado I. G., J. Mol. Catal. B: Enzym., 2007, 49, 18

    Article  CAS  Google Scholar 

  11. Daimon E., Wada I., Akada M., Preparation of 4-Hydroxyphenethyl Alcohols, JP2000327610A, 2000

  12. Yoo S. E., Gong Y. D., Choi M. Y., Seo J. S., Yang Y. K., Tetrahedron Lett., 2000, 41, 6415

    Article  CAS  Google Scholar 

  13. Bodnar B. S., Vogt P. F., J. Org. Chem., 2009, 74, 2598

    Article  CAS  Google Scholar 

  14. Toyao T., Siddiki S. M. A. H., Morita Y., Kamachi T., Touchy A. S., Onodera W., Kon K., Furukawa S., Ariga H., Asakura K., Yoshizawa K., Shimizu K.-I., Chem. Eur. J., 2017, 23, 14848

    Article  CAS  Google Scholar 

  15. Baruah R. N., Tetrahedron Lett., 1992, 33, 5417

    Article  CAS  Google Scholar 

  16. Goswami A., Borthakur N., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 1994, 33B, 495

    CAS  Google Scholar 

  17. Bai Y., Bi H., Zhuang Y., Liu C., Cai T., Liu X., Zhang X., Liu T., Ma Y., Scientific Reports, 2014, 4, 6640

    Article  CAS  Google Scholar 

  18. Bianco A., Passacantilli P., Righi G., Synth. Commun., 1988, 18, 1765

    Article  CAS  Google Scholar 

  19. Guziec F. S. Jr., Wei D., Tetrahedron Lett., 1992, 33, 7465

    Article  CAS  Google Scholar 

  20. Notomista E., Scognamiglio R., Troncone L., Donadio G., Pezzella A., Di Donato A., Izzo V., Appl. Environ. Microbiol., 2011, 77, 5428

    Article  CAS  Google Scholar 

  21. Sysolyatin S. V., Kryukov Y. A., Malykhin V. V., Muradov K. K., Chernysheva G. A., Aliev O. I., Smol’yakova V. I., Anishchenko A. M., Sidekhmenova A. V., Shamanaev A. Y., Plotnikov M. B., Russ. Chem. Bull., 2015, 64, 2210

    Article  CAS  Google Scholar 

  22. Zubarovskii V. M., Verbovskaya T. M., Kiprianov A. I., Zh. Obshch. Khim., 1961, 31, 3056

    CAS  Google Scholar 

  23. Misal Castro L. C., Li H., Sortais J. B., Darcel C., Chem. Commun., 2012, 48, 10514

    Article  CAS  Google Scholar 

  24. Fernandez-Pastor I., Fernandez-Hernandez A., Rivas F., Martinez A., Garcia-Granados A., Parra A., Journal of Natural Products, 2016, 79, 1737

    Article  CAS  Google Scholar 

  25. Zhou Y., Gao G., Li H., Qu J., Tetrahedron Lett., 2008, 49, 3260

    Article  CAS  Google Scholar 

  26. Liang Y. N., Oh W. D., Li Y. M., Hu X., Appl. Catal. A, 2018, 562, 94

    Article  CAS  Google Scholar 

  27. Iglesias D., Melchionna M., Catalysts, 2019, 9, 128/1

    Article  CAS  Google Scholar 

  28. Zhang L. H., Shi Y. M., Zhang L. H., Shiju N. R., Wang Y., Adv. Sci., 2020, 7, 1902126

    Article  CAS  Google Scholar 

  29. Udin I., Shaharun M. S., Naeem A., Alotaibi M. A., Alharthi A. I., Bakht M. A., Nasir Q., Ceram. Int., 2020, 46, 18446

    Article  CAS  Google Scholar 

  30. Chen W. M., Zhang Y., Zhu Z. Y., Chem. Res. Chinese Universities., 2019, 35(1), 133

    Article  CAS  Google Scholar 

  31. Yan B. L., Liu D. P., Feng X. L., Shao M. Z., Zhang Y., Chem. Res. Chinese Universities, 2020, 36(3), 425

    Article  CAS  Google Scholar 

  32. Yu F. Y., Wang K., Wang C., He X. X., Liao Y., Zhao S. L., Mao H., Li X. T., Ma J., Chem. Res. Chinese Universities, 2020, 36(6), 1332

    Article  CAS  Google Scholar 

  33. Mierczynski P., Vasilev K., Mierczynska A., Maniukiewicz W., Szynkowska M. I., Maniecki T. P., Appl. Catal. B: Environ., 2016, 185, 281

    Article  CAS  Google Scholar 

  34. Gravel E., Namboothiri I. N. N., Doris E., Synlett, 2016, 27, 1179

    Article  CAS  Google Scholar 

  35. Vanyorek L., Halasi G., Pekker P., Kristaly F., Konya Z., Catal. Lett., 2016, 146, 2268

    Article  CAS  Google Scholar 

  36. Markiton M., Szelwicka A., Boncel S., Jurczyk S., Chrobok A., Appl. Catal. A: Gen., 2018, 556, 81

    Article  CAS  Google Scholar 

  37. Shi L., Chen Z., Jian Z., Guo F., Gao C., International Journal of Hydrogen Energy, 2019, 44, 19868

    Article  CAS  Google Scholar 

  38. Łamacz A., Jagódka P., Stawowy M., Matus K., Catalysts, 2020, 10(7), 741

    Article  Google Scholar 

  39. Wang G. N., Chen L. M., Sun Y. H., Wu J. L., Fu M. L., Ye D. Q., RSC Adv., 2015, 5, 45320

    Article  CAS  Google Scholar 

  40. Pouilloux Y., Autin F., Guimon C., Barrault J., Journal of Catalysis, 1998, 176, 215

    Article  CAS  Google Scholar 

  41. Zhang J., Leitus G., Ben-David Y., Milstein D., Angew. Chem. Int. Ed., 2006, 45, 1113

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No.21773196).

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Authors and Affiliations

  1. State Key Laboratory of Physical Chemistry of Solid Surfaces, National Engineering Laboratory for Green Chemical Productions of Alcohols, Ethers and Esters, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, P. R. China

    Xin Dong, Xi Chen & Zhaohui Zhou

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  1. Xin Dong
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  2. Xi Chen
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  3. Zhaohui Zhou
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Correspondence to Xin Dong.

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40242_2021_446_MOESM1_ESM.pdf

Efficient synthesis of p-hydroxyphenyl ethanol from hydrogenation of methyl p-hydroxyphenylacetate with CNTs-promoted Cu-Zr catalyst

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Dong, X., Chen, X. & Zhou, Z. Efficient Synthesis of p-Hydroxyphenyl Ethanol from Hydrogenation of Methyl p-Hydroxyphenylacetate with CNTs-promoted Cu-Zr Catalyst. Chem. Res. Chin. Univ. 37, 745–750 (2021). https://doi.org/10.1007/s40242-021-0446-6

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  • DOI: https://doi.org/10.1007/s40242-021-0446-6

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