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

doi:10.1007/s40242-021-0446-6

Abstract

Abstract: Hydrogenation of methyl p-hydroxyphenylacetate has been used for the synthesis of p-hydroxyphenyl ethanol. The reaction was catalyzed by Cu_iZr_j-x%(mass fraction) carbon nanotubes(CNTs) catalysts. Incorporation of a minor amount of CNTs into Cu_iZr_j 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.

Key words: p-Hydroxyphenyl ethanol synthesis, Hydrogenation, Methyl p-hydroxyphenylacetate, Carbon nanotube, Catalyst of Cu_iZr_j-x%CNTs

DONG Xin, CHEN Xi, ZHOU Zhaohui. Efficient Synthesis of p-Hydroxyphenyl Ethanol from Hydrogenation of Methyl p-Hydroxyphenylacetate with CNTs-promoted Cu-Zr Catalyst[J]. Chemical Research in Chinese Universities, 2021, 37(3): 745-750.

References 41

[1]	Brown H. C., Narasimhan S., Choi Y. M., J. Org. Chem., 1982, 47, 4702
[2]	Chen P., Zhang H. B., Lin G. D., Hong Q., Tsai K. R., Carbon, 1997, 35, 1495
[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
[4]	Venkateswarlu S., Panchagnula G. K., Subbaraju G. V., Indian J. Chem., Sect. B:Org. Chem. Incl. Med. Chem., 2006, 45B, 1063
[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
[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
[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
[8]	Alvarez Calero J. M., Jorge Z. D., Massanet G. M., Org. Lett., 2016, 18, 6344
[9]	Brenna E., Fronza G., Fuganti C., Pinciroli M., Journal of Agricultural and Food Chemistry, 2003, 51, 4866
[10]	Pinedo-Rivilla C., Aleu J., Collado I. G., J. Mol. Catal. B:Enzym., 2007, 49, 18
[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
[13]	Bodnar B. S., Vogt P. F., J. Org. Chem., 2009, 74, 2598
[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
[15]	Baruah R. N., Tetrahedron Lett., 1992, 33, 5417
[16]	Goswami A., Borthakur N., Indian J. Chem., Sect. B:Org. Chem. Incl. Med. Chem., 1994, 33B, 495
[17]	Bai Y., Bi H., Zhuang Y., Liu C., Cai T., Liu X., Zhang X., Liu T., Ma Y., Scientific Reports, 2014, 4, 6640
[18]	Bianco A., Passacantilli P., Righi G., Synth. Commun., 1988, 18, 1765
[19]	Guziec F. S. Jr., Wei D., Tetrahedron Lett., 1992, 33, 7465
[20]	Notomista E., Scognamiglio R., Troncone L., Donadio G., Pezzella A., Di Donato A., Izzo V., Appl. Environ. Microbiol., 2011, 77, 5428
[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
[22]	Zubarovskii V. M., Verbovskaya T. M., Kiprianov A. I., Zh. Obshch. Khim., 1961, 31, 3056
[23]	Misal Castro L. C., Li H., Sortais J. B., Darcel C., Chem. Commun., 2012, 48, 10514
[24]	Fernandez-Pastor I., Fernandez-Hernandez A., Rivas F., Martinez A., Garcia-Granados A., Parra A., Journal of Natural Products, 2016, 79, 1737
[25]	Zhou Y., Gao G., Li H., Qu J., Tetrahedron Lett., 2008, 49, 3260
[26]	Liang Y. N., Oh W. D., Li Y. M., Hu X., Appl. Catal. A, 2018, 562, 94
[27]	Iglesias D., Melchionna M., Catalysts, 2019, 9, 128/1
[28]	Zhang L. H., Shi Y. M., Zhang L. H., Shiju N. R., Wang Y., Adv. Sci., 2020, 7, 1902126
[29]	Udin I., Shaharun M. S., Naeem A., Alotaibi M. A., Alharthi A. I., Bakht M. A., Nasir Q., Ceram. Int., 2020, 46, 18446
[30]	Chen W. M., Zhang Y., Zhu Z. Y., Chem. Res. Chinese Universities., 2019, 35(1), 133
[31]	Yan B. L., Liu D. P., Feng X. L., Shao M. Z., Zhang Y., Chem. Res. Chinese Universities, 2020, 36(3), 425
[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
[33]	Mierczynski P., Vasilev K., Mierczynska A., Maniukiewicz W., Szynkowska M. I., Maniecki T. P., Appl. Catal. B:Environ., 2016, 185, 281
[34]	Gravel E., Namboothiri I. N. N., Doris E., Synlett, 2016, 27, 1179
[35]	Vanyorek L., Halasi G., Pekker P., Kristaly F., Konya Z., Catal. Lett., 2016, 146, 2268
[36]	Markiton M., Szelwicka A., Boncel S., Jurczyk S., Chrobok A., Appl. Catal. A:Gen., 2018, 556, 81
[37]	Shi L., Chen Z., Jian Z., Guo F., Gao C., International Journal of Hydrogen Energy, 2019, 44, 19868
[38]	Łamacz A., Jagódka P., Stawowy M., Matus K., Catalysts, 2020, 10(7), 741
[39]	Wang G. N., Chen L. M., Sun Y. H., Wu J. L., Fu M. L., Ye D. Q., RSC Adv., 2015, 5, 45320
[40]	Pouilloux Y., Autin F., Guimon C., Barrault J., Journal of Catalysis, 1998, 176, 215
[41]	Zhang J., Leitus G., Ben-David Y., Milstein D., Angew. Chem. Int. Ed., 2006, 45, 1113