Sonochemical and Mechanochemical Synthesis of Alcohols from Aldehydes and Ketones
Indah Mutiara Putri(1), Ferlana Debbora Dachi(2), Dhina Fitriastuti(3), Muhammad Idham Darussalam Mardjan(4*)
(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Islam Indonesia, Jl. Kaliurang km. 14, Yogyakarta 55584, Indonesia
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia
(*) Corresponding Author
Abstract
Keywords
Full Text:
Full Text PDFReferences
[1] Scognamiglio, J., Jones, L., Vitale, D., Letizia, C.S., and Api, A.M., 2012, Fragrance material review on benzyl alcohol, Food Chem. Toxicol., 50, S140–S160.
[2] Xu, J., Liu, N., Zou, L., Cheng, F., Shen, X., Liu, T., Lv, H., Khan, R., and Fan, B., 2019, Visible-light driven hydrolysis of benzyl halides with water for preparation of benzyl alcohols, Asian J. Org. Chem., 8 (2), 261–264.
[3] Li, J., Wang, H., Liu, L., and Sun, J., 2014, Metal-free, visible-light photoredox catalysis: Transformation of arylmethyl bromides to alcohols and aldehydes, RSC Adv., 4 (91), 49974–49978.
[4] Chen, Y., Hu, J., and Ding, A., 2020, Aerobic photooxidative hydroxylation of boronic acids catalyzed by anthraquinone-containing polymeric photosensitizer, RSC Adv., 10 (13), 7927–7932.
[5] Ding, A., Zhang, Y., Chen, Y., Rios, R., Hu, J., and Guo, H., 2019, Visible light induced oxidative hydroxylation of boronic acids, Tetrahedron Lett., 60 (9), 660–663.
[6] Park, J., Lee, Y.M., Nam, W., and Fukuzumi, S., 2013, Brønsted acid-promoted C–H bond cleavage via electron transfer from toluene derivatives to a protonated nonheme iron(IV)-oxo complex with no kinetic isotope effect, J. Am. Chem. Soc., 135 (13), 5052–5061.
[7] Voronin, V.V., Ledovskaya, M.S., Rodygin, K.S., and Ananikov, V.P., 2020, Examining the vinyl moiety as a protecting group for hydroxyl (–OH) functionality under basic conditions, Org. Chem. Front., 7 (11), 1334–1342.
[8] Li, X.G., Li, F., Xu, Y., Xiao, L.J., Xie, J.H., and Zhou, Q.L., 2022, Hydrogenation of esters by manganese catalysts, Adv. Synth. Catal., 364 (4), 744–749.
[9] Wang, F., Tan, X., Lv, H., and Zhang, X, 2016, New ruthenium complexes based on tetradentate bipyridine ligands for catalytic hydrogenation of esters, Chem. - Asian J., 11 (15), 2103–2106.
[10] Gonzalez-de-Castro, A., Cosimi, E., Aguila, M.J.B., Gajewski, P., Schmitkamp, M., de Vries, J.G., and Lefort, L., 2017, Long-chain α–ω diols from renewable fatty acids via tandem olefin metathesis–ester hydrogenation, Green Chem., 19 (7), 1678–1684.
[11] Kawano, T., Watari, R., Kayaki, Y., and Ikariya, T., 2019, Catalytic hydrogenation of carboxamides with a bifunctional Cp*Ru catalyst bearing an imidazol-2-ylidene with a protic aminoethyl side chain, Synthesis, 51 (12), 2542–2547.
[12] Cabrero-Antonino, J.R., Alberico, E., Drexler, H.J., Baumann, W., Junge, K., Junge, H., and Beller, M., 2016, Efficient base-free hydrogenation of amides to alcohols and amines catalyzed by well-defined pincer imidazolyl–ruthenium complexes, ACS Catal., 6 (1), 47–54.
[13] Tavakoli, G., and Prechtl, M.H.G., 2019, The reductive deaminative conversion of nitriles to alcohols using para-formaldehyde in aqueous solution, Catal. Sci. Technol., 9 (21), 6092–6101.
[14] He, J., Xu, Y., Yu, Z., Li, H., Zhao, W., Wu, H., and Yang, S., 2020, ZrOCl2 as a bifunctional and in situ precursor material for catalytic hydrogen transfer of bio-based carboxides, Sustainable Energy Fuels, 4 (6), 3102–3114.
[15] Neyt, N.C., and Riley, D.L., 2018, Mild and selective reduction of aldehydes utilising sodium dithionite under flow conditions, Beilstein J. Org. Chem., 14, 1529–1536.
[16] Mandal, T., Jana, S., and Dash, J., 2017, Zinc-mediated efficient and selective reduction of carbonyl compounds: zinc-mediated efficient and selective reduction of carbonyl compounds, Eur. J. Org. Chem., 2017 (33), 4972–4983.
[17] Zhao, W., Meier, S., Yang, S., and Riisager, A., 2020, Ammonia borane enabled upgrading of biomass derivatives at room temperature, Green Chem., 22 (18), 5972–5977.
[18] Mohanty, A.D., and Bae, C., 2014, Mechanistic analysis of ammonium cation stability for alkaline exchange membrane fuel cells, J. Mater. Chem. A, 2 (41), 17314–17320.
[19] Shahinnoranikoliji, S., and Khezri, B., 2015, Reduction of carbonyl compounds with Zn(BH4)2 under microwave irradiation, Orient. J. Chem., 31 (4), 2449–2451.
[20] Cao, J., Ma, C., Zang, J., Gao, S., Gao, Q., Kong, X., Yan, Y., Liang, X., Ding, Q., Zhao, C., Wang, B., Xu, W., and Zhang, Y., 2018, Novel leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry, Bioorg. Med. Chem., 26 (12), 3145–3157.
[21] Abdullaha, M., Ali, M., Kour, D., Mudududdla, R., Khajuria, P., Kumar, A., and Bharate, S.B., 2021, Tetramethoxystilbene inhibits NLRP3 inflammasome assembly via blocking the oligomerization of apoptosis-associated speck-like protein containing caspase recruitment domain: in vitro and in vivo evaluation, ACS Pharmacol. Transl. Sci., 4 (4), 1437–1448.
[22] Sri Ramya, P.V., Angapelly, S., Guntuku, L., Singh Digwal, C., Nagendra Babu, B., Naidu, V.G.M., and Kamal, A., 2017, Synthesis and biological evaluation of curcumin inspired indole analogues as tubulin polymerization inhibitors, Eur. J. Med. Chem., 127, 100–114.
[23] Chatel, G., and Varma, R.S., 2019, Ultrasound and microwave irradiation: contributions of alternative physicochemical activation methods to Green Chemistry, Green Chem., 21 (22), 6043–6050.
[24] Mardjan, M.I.D., Hariadi, M.F., Putri, I.M., Musyarrofah, N.A., Salimah, M., Priatmoko, P., Purwono, B., and Commeiras, L., 2022, Ultrasonic-assisted-synthesis of isoindolin-1-one derivatives, RSC Adv., 12 (29), 19016–19021.
[25] Martínez, R.F., Cravotto, G., and Cintas, P., 2021, Organic sonochemistry: A chemist's timely perspective on mechanisms and reactivity, J. Org. Chem., 86 (20), 13833–13856.
[26] Varma, R.S., 2016, Greener and sustainable trends in synthesis of organics and nanomaterials, ACS Sustainable Chem. Eng., 4 (11), 5866–5878.
[27] da Silveira Pinto, L., and de Souza, M., 2017, Sonochemistry as a General Procedure for the Synthesis of Coumarins, Including Multigram Synthesis, Synthesis, 49 (12), 2677–2682.
[28] Liu, X., Li, Y., Zeng, L., Li, X., Chen, N., Bai, S., He, H., Wang, Q., and Zhang, C., 2022, A Review on mechanochemistry: Approaching advanced energy materials with greener force, Adv. Mater., 34 (46), 2108327.
[29] Fitriastuti, D., Mardjan, M.I.D., Jumina, J., and Mustofa, M., 2014, Synthesis and heme polymerization inhibitory activity (HPIA) assay of antiplasmodium of (1)-N-(3,4-dimethoxybenzyl)-1,10-phenanthrolinium bromide from vanillin, Indones. J. Chem., 14 (1), 1–6.
[30] Chavan, P.N., Pansare, D.N., and Shelke, R.N., 2019, Eco-friendly, ultrasound-assisted, and facile synthesis of one-pot multicomponent reaction of acridine-1,8(2H,5H)-diones in an aqueous solvent, J. Chin. Chem. Soc., 66 (8), 822–828.
[31] Dachi, F.D., 2022, Pengaruh sterik dan induksi benzaldehida terhadap sintesis turunan benzil alkohol melalui reaksi reduksi menggunakan metode sonokimia, Undergraduate Thesis, Universitas Gadjah Mada, Yogyakarta.
[32] Tanemura, K., 2022, Reduction of aldehydes and ketones by a stoichiometric amount of NaBH4 using a small amount of MeOH or EtOH, Results Chem., 4, 100486.
[33] Pagola, S., 2023, Outstanding advantages, current drawbacks, and significant recent developments in mechanochemistry: a perspective view, Crystals, 13 (1), 124.
DOI: https://doi.org/10.22146/ijc.82943
Article Metrics
Abstract views : 1451 | views : 921Copyright (c) 2023 Indonesian Journal of Chemistry
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.
View The Statistics of Indones. J. Chem.