Solvent free selective acylation of phenol by HF–modified saponite catalysts

Albadi, 2015, Efficient approach for the chemoselective acetylation of alcohols catalyzed by a novel metal oxide nanocatalyst CuO-ZnO, Chin. J. Catal., 36, 308, 10.1016/S1872-2067(14)60259-X Alleti, 2005, Gadolinium triflate: an efficient and convenient catalyst for acetylation of alcohols and amines, J. Mol. Catal. A, 226, 57, 10.1016/j.molcata.2004.09.024 Anbu, 2019, Acetylation of alcohols, amines, phenols, thiols under catalyst and solvent-free conditions, Chemistry, 1, 69, 10.3390/chemistry1010006 Belzunce, 1998, Modification of sepiolite by treatment with fluorides: structural and textural changes, Clay Clay Miner., 46, 603, 10.1346/CCMN.1998.0460601 Bieseki, 2013, Acid treatments of montmorillonite-rich clay for Fe removal using a factorial design method, Mater. Res., 16, 1122, 10.1590/S1516-14392013005000114 Chakraborti, 2003, Indium (III) chloride as a new, highly efficient, and versatile catalyst for acylation of phenols, thiols, alcohols, and amines, Tetrahedron Lett., 44, 6749, 10.1016/S0040-4039(03)01641-1 Chakraborti, 2004, Zirconium (IV) chloride as a new, highly efficient, and reusable catalyst for acetylation of phenols, thiols, amines, and alcohols under solvent-free conditions, Synlett, 627, 10.1055/s-2004-815442 Chandra, 2002, Lewis acid catalyzed acylation reactions: scope and limitations, Tetrahedron, 58, 1369, 10.1016/S0040-4020(01)01229-7 Chouke, 2015, Solvent free synthesis of p-hydroxyacetophenone in a situ using eco-friendly catalyst in Fries rearrangement, J. Chem. Pharm. Res., 7, 727 Das, 2011, Silver triflate catalyzed acetylation of alcohols, thiols, phenols, and amines, Synthesis, 42, 1621 De, 2004, Ruthenium (III) chloride catalyzed acylation of alcohols, phenols, thiols, and amines, Tetrahedron Lett., 45, 2919, 10.1016/j.tetlet.2004.02.071 Fraser, 2002, Use of hydrofluoric acid dissolution for the concentration of dickite and nacrite from kaolin deposits: an FTIR study, Clay Miner., 37, 559, 10.1180/0009855023730058 Gidley, 1985, Acidizing sandstone formations: a detailed examination of recent experience Gul, 2002, Antimicrobial evaluation of some Mannich bases of acetophenones and representative quaternary derivatives, Arzneimittelforschung, 52, 773 Jabłońska, 2019, Natural and chemically modified post-mining clays—Structural and surface properties and preliminary tests on copper sorption, Minerals., 9, 704, 10.3390/min9110704 Kamal, 2007, Al(OTf)3 as a highly efficient catalyst for the rapid acetylation of alcohols, phenols and thiophenols under solvent-free conditions, Tetrahedron Lett., 48, 3813, 10.1016/j.tetlet.2007.03.162 Komadel, 2016, Acid activated clays: Materials in continuous demand, Appl. Clay Sci., 131, 84, 10.1016/j.clay.2016.05.001 Komadel, 2013, Acid activation of clay minerals, 385, 10.1016/B978-0-08-098258-8.00013-4 Kong, 2014, Effects of oxalic and citric acids on three clay minerals after incubation, Appl. Clay Sci., 99, 207, 10.1016/j.clay.2014.06.035 2002 Kozhevnikov, 2003, Friedel–Crafts acylation and related reactions catalysed by heteropoly acids, Appl. Catal. A Gen., 256, 3, 10.1016/S0926-860X(03)00406-X Liu, 2014, 4-(N, N-Dimethylamino) pyridine hydrochloride as a recyclable catalyst for acylation of inert alcohols: substrate scope and reaction mechanism, Org. Lett., 16, 236, 10.1021/ol4030875 Lopez, 2011, Task-oriented use of ionic liquids: efficient acetylation of alcohols and phenols, Tetrahedron Lett., 52, 3339, 10.1016/j.tetlet.2011.04.079 Mackenzie, 1970 Marosz, 2020, Acid-treated clay minerals as catalysts for dehydration of methanol and ethanol, Clay Clay Miner., 68, 23, 10.1007/s42860-019-00051-y Mott, 1986 Mulla, 2012, Highly efficient cobalt (II) catalyzed o-acylation of alcohols and phenols under solvent-free conditions, OJSTA, 1, 31, 10.4236/ojsta.2012.13006 Murray, 2006, Structure and composition of the clay minerals and their physical and chemical properties, 7, 10.1016/S1572-4352(06)02002-2 Nagendrappa, 2002, Organic synthesis using clay catalysts: clays for ‘Green Chemistry.’, Reson., 7, 10.1007/BF02836172 Prieto, 1999, Study of the porous solids obtained by acid treatment of a high surface area saponite, J. Porous. Mater., 6, 335, 10.1023/A:1009657312123 Rajabi, 2005, Acetophenones with selective antimycobacterial activity, Lett. Appl. Microbiol., 40, 212, 10.1111/j.1472-765X.2005.01657.x Ranu, 2003, Highly efficient acylation of alcohols, amines and thiols under solvent-free and catalyst-free conditions, Green Chem., 5, 44, 10.1039/b211238h Roswanda, 2018, A Straightforward Selective Acylation of Phenols over ZSM-5 towards making Paracetamol Precursors, Bull. Chem. React. Eng. Catal., 13, 573, 10.9767/bcrec.13.3.2856.573-587 Sheldon, 2001 Singh, 2014, A synthesis of copper based metal-organic framework for O-acetylation of alcohols, Catal. Commun., 44, 24, 10.1016/j.catcom.2013.10.016 Tachrim, 2017, Trifluoromethanesulfonic acid as acylation catalyst: special feature for C- and/or O-acylation reactions, Catalysts., 7, 40, 10.3390/catal7020040 Thommes, 2015, Physisorption of gases, with special reference to the evaluation of surface area and pore size distribution (IUPAC Technical Report), Pure Appl. Chem., 87, 1051, 10.1515/pac-2014-1117 Trivedi, 2015, Evaluation of physical, thermal and spectroscopic properties of biofield treated p-hydroxyacetophenone, Nat. Prod. Res., 3, 190 Tsai, 2006, Characterization and adsorption properties of diatomaceous earth modified by hydrofluoric acid etching, J. Colloid Interface Sci., 297, 749, 10.1016/j.jcis.2005.10.058 Veisi, 2016, Preparation of polydopamine sulfamic acid-functionalized magnetic Fe3O4 nanoparticles with a core/shell nanostructure as heterogeneous and recyclable nanocatalysts for the acetylation of alcohols, phenols, amines and thiols under solvent-free conditions, Green Chem., 18, 6337, 10.1039/C6GC01975G Vellayan, 2018, Pd supported on Cu-doped Ti-pillared montmorillonite as catalyst for the Ullmann coupling reaction, Appl. Clay Sci., 160, 126, 10.1016/j.clay.2017.12.037 Vicente, 2013, 523 Vicente-Rodríguez, 1996, Comparative FT-IR study of the removal of octahedral cations and structural modifications during acid treatment of several silicates, Spectrochim. Acta A, 52, 1685, 10.1016/S0584-8539(96)01771-0 Wang, 1995, Regioselective acylation of anisole with carboxylic acids over HZSM-5 catalyst, J. Chem. Soc., Chem, 22, 2307, 10.1039/c39950002307 Wuts, 2006 Zhang, 2007, Metal-and solvent-free conditions for the acylation reaction catalyzed by carbon tetrabromide (CBr4), Green Chem., 9, 1022, 10.1039/b702646c Zhou, 2016, Phosphonic-based hydrofluoric acid: interactions with clay minerals and flow in sandstone cores, SPE J., 21, 264, 10.2118/164472-PA Zhou, 2019, Modification, hybridization and applications of saponite: an overview, Appl. Clay Sci., 168, 136, 10.1016/j.clay.2018.11.002