- Nitration method for p-alkylphenol
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The invention discloses a nitration method for p-alkylphenol. The nitration method successively comprises the following steps: 1) adding the p-alkylphenol used as a raw material into a container, thenadding water and a catalyst, dropwise adding nitric acid under stirring, controlling a temperature of materials in the container not to exceed 25 DEG C in the dropwise adding process, and after the nitric acid is dropwise added, carrying out a reaction at 10 to 20 DEG C for 2 to 3 h; and 2) subjecting a reaction solution obtained in the step 1) to standing and layering, wherein the lower layer obtained by layering is a product (o-nitro-p-alkylphenol), and subjecting an upper-layer solution obtained by layering to cyclic reuse, i.e., cyclic nitration. By adoption of the method for synthesizingthe o-nitro-p-alkylphenol provided by the invention, the utilization rate of raw materials is high; cyclic reuse of waste acid and waste water is realized; the discharging of three wastes is reduced;the cost of production is lowered; meanwhile, a product has high purity, high yield and good industrial application value.
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Paragraph 0063-0067
(2019/04/10)
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- Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation
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The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.
- Juárez-Ornelas, Kevin A.,Jiménez-Halla, J. Oscar C.,Kato, Terumasa,Solorio-Alvarado, César R.,Maruoka, Keiji
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supporting information
p. 1315 - 1319
(2019/03/07)
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- Nitration method for aryl phenol or aryl ether derivative
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The invention relates to a nitration method for an aryl phenol or aryl ether derivative. The method comprises the steps of stirring an aryl phenol or aryl ether compound, nitrate, trimethylchlorosilane (TMSCl) and a copper salt in an acetonitrile solution in air at room temperature, simultaneously, monitoring extent of reaction through a TLC dot plate, removing a solvent from a mixture by a rotaryevaporator after a substrate is consumed completely, and carrying out purification through a silica-gel column, thereby obtaining a nitroolefin derivative. Meanwhile, the selective mono-nitration orbis-nitration of the substrate can be achieved through controlling equivalent weight of the nitrate. Compared with the prior art, the nitration method disclosed by the invention has the advantages that the consumption of strong-acid substances is avoided, the reaction conditions are mild, the yield is high, the applicable range of the substrate is wide, reaction activity is free of obvious attenuation after an amplified reaction, and an excellent yield is still obtained, so that the method has an obvious industrial application value.
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Paragraph 0050-0055; 0068-0070
(2020/01/03)
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- A new method for the mononitration of phenol derivatives by poly(4-vinylpyridinium nitrate) and silica sulfuric acid under mild conditions
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This procedure works efficiently for high selective mono nitration of phenol and substituted phenol to corresponding nitro compounds in moderate to high yield using poly(4-vinylpyridinium nitrate) and silica sulfuric acid in dichloromethane at room temperature.
- Goudarziafshar, Hamid
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experimental part
p. 458 - 461
(2012/06/18)
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- A mild procedure for the preparation of o-nitrophenols by nitro urea or ammonium nitrate in the presence of silica sulfuric acid (SiO 2-OSO3H)
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A mixture of ammonium nitrate or nitro urea and silica sulfuric acid was found to be efficient and environmentally friendly nitrating media for the preparation of orto-nitro phenols in dichloromethane at room temperature. A mixture of ammonium nitrate or nitro urea and silica sulfuric acid was found to be efficient and environmentally friendly nitrating media for the preparation of orto-nitro phenols in dichloromethane at room temperature.
- Ghorbani-Choghamarani, Arash,Nikoorazm, Mohsen,Goudarziafshar, Hamid,Naserifar, Zahra,Zamani, Parisa
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experimental part
p. 731 - 734
(2011/11/12)
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- Mononitration of phenol derivatives by guanidinium nitrate and silica sulfuric acid under mild conditions
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A mixture of guanidinium nitrate and silica sulfuric acid acts as mild and heterogeneous media for the efficient mono nitration of phenolic compounds in dichloromethane at room temperature.
- Ghorbani-Choghamarani, Arash,Goudarziafshar, Hamid,Nikoorazm, Mohsen,Naseri, Zahra
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experimental part
p. 1431 - 1434
(2012/06/01)
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- HARMFUL ARTHROPOD CONTROL COMPOSITION, AND FUSED HETEROCYCLIC COMPOUND
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Disclosed is a harmful arthropod control composition comprising, as an active ingredient, a fused heterocyclic compound represented by formula (1) [wherein A1 and A2 independently represent a nitrogen atom or the like; R1 and R4 independently represent a halogen atom or the like; R2 and R3 independently represent a halogen atom or the like; R5 and R6 independently represent a linear C1-C6 hydrocarbon group which may be substituted, or the like (provided that both R5 and R6 cannot represent a hydrogen atom simultaneously); and n represents 0 or 1]. The harmful arthropod control composition has an excellent efficacy to control harmful arthropods.
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Page/Page column 120-121
(2011/02/18)
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- HARMFUL ARTHROPOD CONTROL COMPOSITION, AND FUSED HETEROCYCLIC COMPOUND
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Disclosed is a harmful arthropod control composition comprising, as an active ingredient, a fused heterocyclic compound represented by formula (1) [wherein A1 and A2 independently represent a nitrogen atom or the like; R1 and R4 independently represent a halogen atom or the like; R2 and R3 independently represent a halogen atom or the like; R5 and R6 independently represent a linear C1-C6 hydrocarbon group which may be substituted, or the like (provided that both R5 and R6 cannot represent a hydrogen atom simultaneously); and n represents 0 or 1]. The harmful arthropod control composition has an excellent efficacy to control harmful arthropods.
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Page/Page column 75-76
(2011/04/13)
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- COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
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The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a neonicotinoid compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a neonicotinoid compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
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Page/Page column 201
(2011/04/25)
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- COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
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The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a pyrethroid compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a pyrethroid compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
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Page/Page column 201
(2011/05/06)
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- COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
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The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and pyriproxyfen; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and pyriproxyfen to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
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Page/Page column 200
(2011/05/06)
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- COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
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The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and pyridalyl; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and pyridalyl to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
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Page/Page column 200
(2011/05/06)
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- COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
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The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a diamide compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a diamide compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
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Page/Page column 204
(2011/05/06)
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- Aluminum nitrate and silica sulfuric acid as efficient nitrating media for the mononitration of phenols under mild and heterogeneous conditions
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A variety of phenol derivatives were successfully nitrated via combination of Al(NO3)3-9H2O and silica sulfuric acid in the presence of wet SiO2 (50% w/w) in dichloromethane at room temperature with moderate-to-good yields.
- Ghorbani-Choghamarani, Arash,Goudarziafshar, Hamid,Nikoorazm, Mohsen,Yousefi, Somaieh
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experimental part
p. 1144 - 1147
(2009/10/23)
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- Nitration of phenolic compounds by metal-modified montmorillonite KSF
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The nitration of phenolic compounds with 60% nitric acid (1.2 equiv) has been carried out in the presence of metal-modified montmorillonite KSF, prepared from different metals (V, Mo, W; Sc, La, Yb, Eu, In, Bi, Ti, Zr, Hf) and KSF or nitric acid treated HKSF, as catalysts. These catalysts showed good stabilities and high catalytic activities in nitration process. In addition, these catalysts can be recovered easily and reused for many times in nitration. This process is an eco-safer and environment-benign way for clean synthesis of nitrated phenolic compounds.
- Yin, Wan-Po,Shi, Min
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p. 10861 - 10867
(2007/10/03)
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- Microwave assisted synthesis of 4-alkyl-2-([5-substituted-2-hydroxyphenyl]- iminomethyl)benzenols and their NMR characterization
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Imines, 4-alkyl-2-([5-substituted-2-hydroxyphenyl]iminomethyl)-benzenols 1, have been obtained successfully in excellent yield from the corresponding aldehydes and amines by microwave irradiation. The resultant Schiff bases have been fully characterized by spectral data.
- Sridharan,Muthusubramanian,Sivasubramanian
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p. 416 - 419
(2007/10/03)
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- A New Method for Nitration of Phenolic Compounds
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Phenolic compounds can be nitrated by 65% nitric acid in the presence of catalytic amounts of montmorillonite KSF and bismuth(III) nitrate to give the corresponding nitrated products in good yields in a heterogeneous phase. The co-catalyst of KSF and Bi(NO3)3 can be easily recovered and reused in the next batch of nitration.
- Shi, Min,Cui, Shi-Cong
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p. 1197 - 1202
(2007/10/03)
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- O-nitrophenyltriflates in quinoline synthesis : Easy access to a streptonigrin synthon
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An efficient route to a wide range of 2-hydroxyquinolines from o-nitrophenyltriflates via a Heck reaction is reported, with emphasis on the preparation of a synthetic equivalent of the streptonigrin AB ring system.
- Holzapfel, Cedric W.,Dwyer, Catherine
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p. 215 - 219
(2007/10/03)
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- An N.M.R. Investigation of Ground-State Polarization of Some Substituted Aromatic Systems
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The previously established n.m.r. method for estimating mobile bond orders was applied to the investigation of ground-state polarization of benzene derivatives with ortho or para pairs of +R/-R substituents, naphthalene and five heteroaromatic systems (furan, thiophen, pyrrole, quinoline and pyrazole).Evidence for significant ground-state polarization which is solvent-independent was found in a number of these systems, especially benzene, pyrrole and pyrazole.
- Collins, Michael J.,Hatton, Paul M.,Sternhell, Sever
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p. 1119 - 1134
(2007/10/02)
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- Alkyl-substituted benzoxazinorifamycin derivative, process for preparing the same and antibacterial agent containing the same
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A novel rifamycin derivative having the formula (I): STR1 wherein X1 is an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 8 carbon atoms; X2 is a hydrogen atom or an alkyl group with 1 to 4 carbon atoms; R1 is hydrogen atom or acetyl group; A is a group represented by the formula: STR2 wherein R2 is an alkyl group with 1 to 4 carbon atoms or an alkoxyalkyl group with 2 to 6 carbon atoms and R3 is an alkyl group with 1 to 6 carbon atoms or an alkoxyalkyl group with 2 to 6 carbon atoms, or a group represented by the formula STR3 wherein STR4 is a 3 to 9 membered cyclic amino group with 2 to 8 carbon atoms, R4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, or salts thereof, a process for preparing the same and antibacterial agents containing the same as an effective ingredient. The rifamycin derivative of the present invention having the formula (I) shows a strong antibacterial activity against the Gram-positive bacteria and the acid-fast bacteria.
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- Formation of 4-Nitrocyclohexa-2,5-dienols by Addition of Organolithium Reagents to 4-Alkyl-4-nitrocyclohexa-2,5-dienones
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Addition of methyllithium to 4-alkyl-4-nitrocyclohexa-2,5-dienones 1a-d (alkyl = Me, Et, i-Pr, t-Bu), to 2,6-dichloro- and 2,6-dibromo-4-methyl-4-nitrocyclohexa-2,5-dienone, and to 4a-nitro-2-oxo-2,4a,5,6,7,8-hexahydronaphthalene gives the corresponding dienols 2a-d, 4e and 4f, and 7g, generally as a pair of diastereomers.Addition of methyl lithioacetate to the same substrates gives dienols 8a-d, 5e and 5f, and 7h.Addition of substituted methyllithiums (XCH2Li, X = CN, CONH2, CONMe2, COMe, SMe, SPh, SOMe, SO2Me, SiMe3, PSMePh, PSPh2), 2-lithio-1,3-dithiane, or lithium phenylacetylide to 1a gives the dienols 9i-u.
- Fischer, Alfred,Sankararaman, S.
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p. 4464 - 4468
(2007/10/02)
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- Electrophilic aromatic substitution. Part 24. The nitration of isopropylbenzene, 2- and 4-isopropyltoluene, 1-chloro-4-isopropylbenzene, 4-isopropylanisole, and 2-bromotoluene: Nitrodeisopropylation
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The kinetics and products of nitration in aqueous sulphuric acid of the title compounds have been studied. 4-Isopropyl-phenol and -anisole are nitrated at or near the encounter rate. In 65-79% H2SO4 2-isopropyltoluene suffers ca. 25% ipso-attack; the only fate of W iPri (ipso-Wheland intermediate) is nitrodeisopropylation. From 4-isopropyltoluene WiPri is also nitrodeisopropylated, but some 1,2-nitro-migration may occur. From the same compound WiMe may be captured by water, rearrange, or give 4-methylacetophenone; a mechanism is proposed for the formation of the last compound. Nitrodeisopropylation occurs without the assistance of water. With 4-isopropylanisole, demethoxylation and nitrodeisopropylation are consequences of the formation of WiPri. The results are consistent with increasing attack at C-4 with increasing acidity, loss of isopropyl without assistance from water, and decomposition of the unobserved intermediate, 4-isopropyl-4-nitrocyclohexa-2,5-dienone, by two processes. One, acid-catalysed process gives 4-nitrophenol and possibly 4-isopropyl-2-nitrophenol. The other, probably radical, process gives 4-isopropyl-2-nitrophenol. In contrast to 4-bromotoluene, 2-bromotoluene is not nitrodebrominated.
- Manglik, Ajay K.,Moodie, Roy B.,Schofield, Kenneth,Tobin, Geoffrey D.,Coombes, Robert G.,Hadjigeorgiou, Panicos
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p. 1606 - 1616
(2007/10/02)
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