Abstract:
Hydrolysis of alkyl halides in the presence of copper and its salts in aqueous DMSO (molar ratio organohalide:CuSO4·5H2O:DMSO:H2O = 1:1:10–20:12–25) at 100–117 °C gives alcohols in high yields. Aryl halides containing no activating substituents are inert under the reaction conditions.
Document Type:
Article
Language: English
Citation:
L. G. Menchikov, A. V. Vorogushin, O. S. Korneva, O. M. Nefedov, “An Effective Method for Alcohol Preparation by Hydrolysis of Organohalides in the Presence of Copper and its Salts in Aqueous DMSO”, Mendeleev Commun., 5:6 (1995), 223–224
Linking options:
https://www.mathnet.ru/eng/mendc5110
https://www.mathnet.ru/eng/mendc/v5/i6/p223
This publication is cited in the following 14 articles:
Alejandro Leal-Duaso, Luis Salvatella, José M. Fraile, “Physical-chemical transformations for the remediation and valorization of hexachlorocyclohexanes (HCHs) including lindane: A review”, Journal of Environmental Management, 375 (2025), 124262
Feng-Ping Xia, Yi-Ming Wu, Feng-Zhi Hu, Xiao-Hong Zhang, Xing-Guo Zhang, “Tandem Sulfonylative Annulation/Halogenation of 1,7-Enynes with Sodium Sulfinate and TBAX for the Assembly of 4-Methylenechromanes”, J. Org. Chem., 89:4 (2024), 2351
Fei Wang, Xu‐ling Wang, Li Pan, Bin Wang, Yue‐Sheng Li, “Efficient Copolymerization of Ethylene with Polar Divinyl Monomer by Phosphino‐Phenolate Nickel Catalyst†”, Chin. J. Chem., 41:9 (2023), 1037
Muhammad Gulfam, Sung-Han Jo, Trung Thang Vu, Israr Ali, Ali Rizwan, Soo-Bin Joo, Sang-Hyug Park, Kwon Taek Lim, “NIR-degradable and biocompatible hydrogels derived from hyaluronic acid and coumarin for drug delivery and bio-imaging”, Carbohydrate Polymers, 303 (2023), 120457
Km Kajol, Chintakunta Ramesh, “Sequential One‐pot Method for the Synthesis of 4‐(Hydroxymethyl)oxazoles and their Application in Phosphonates Synthesis”, Asian J Org Chem, 10:3 (2021), 649
Cyril Fersing, Clotilde Boudot, Romain Paoli-Lombardo, Nicolas Primas, Emilie Pinault, Sébastien Hutter, Caroline Castera-Ducros, Youssef Kabri, Julien Pedron, Sandra Bourgeade-Delmas, Alix Sournia-Saquet, Jean-Luc Stigliani, Alexis Valentin, Amaya Azqueta, Damián Muruzabal, Alexandre Destere, Susan Wyllie, Alan H. Fairlamb, Sophie Corvaisier, Marc Since, Aurélie Malzert-Fréon, Carole Di Giorgio, Pascal Rathelot, Nadine Azas, Bertrand Courtioux, Patrice Vanelle, Pierre Verhaeghe, “Antikinetoplastid SAR study in 3-nitroimidazopyridine series: Identification of a novel non-genotoxic and potent anti-T. b. brucei hit-compound with improved pharmacokinetic properties”, European Journal of Medicinal Chemistry, 206 (2020), 112668
Louisa Temme, Frederik Börgel, Dirk Schepmann, Dina Robaa, Wolfgang Sippl, Constantin Daniliuc, Bernhard Wünsch, “Impact of hydroxy moieties at the benzo[7]annulene ring system of GluN2B ligands: Design, synthesis and biological evaluation”, Bioorganic & Medicinal Chemistry, 27:23 (2019), 115146
Haicheng Liu, Jianping Liu, Xiaokai Cheng, Xiaojuan Jia, Lei Yu, Qing Xu, “DMSO‐Triggered Complete Oxygen Transfer Leading to Accelerated Aqueous Hydrolysis of Organohalides under Mild Conditions”, ChemSusChem, 12:13 (2019), 2994
Tobias Hagendorn, Stefan Bräse, “A Route to Cyclooct‐2‐ynol and Its Functionalization by Mitsunobu Chemistry”, Eur J Org Chem, 2014:6 (2014), 1280
Carlos M. R. Abreu, Arménio C. Serra, Anatoliy V. Popov, Krzysztof Matyjaszewski, Tamaz Guliashvili, Jorge F. J. Coelho, “Ambient temperature rapid SARA ATRP of acrylates and methacrylates in alcohol–water solutions mediated by a mixed sulfite/Cu(ii)Br2 catalytic system”, Polym. Chem., 4:23 (2013), 5629
Didier Zurwerra, Florian Glaus, Leo Betschart, Julia Schuster, Jürg Gertsch, Walter Ganci, Karl‐Heinz Altmann, “Total Synthesis of (-)‐Zampanolide and Structure–Activity Relationship Studies on (-)‐Dactylolide Derivatives”, Chemistry A European J, 18:52 (2012), 16868
Umaprasana Ojha, Ritimoni Rajkhowa, Shrikant Rao Agnihotra, Rudolf Faust, “A New General Methodology for the Syntheses of End-Functional Polyisobutylenes by Nucleophilic Substitution Reactions”, Macromolecules, 41:11 (2008), 3832
Stéphane Ledoux, Elisabeth Marchalant, Jean-Pierre Célérier, Gérard Lhommet, “Syntheses from chiral heterocyclic β-amino esters. A new versatile access to pyrrolizidine and quinolizidine alkaloids”, Tetrahedron Letters, 42:32 (2001), 5397
L. G. MENCHIKOV, A. V. VOROGUSHIN, O. S. KORNEVA, O. M. NEFEDOV, “ChemInform Abstract: An Effective Method for Alcohol Preparation by Hydrolysis of Organohalides in the Presence of Copper and Its Salts in Aqueous DMSO.”, ChemInform, 27:16 (1996)