134-11-2Relevant academic research and scientific papers
Copper-mediated direct alkoxylation of arenes using an N, O -bidentate directing system
Zhang, Lin-Bao,Hao, Xin-Qi,Zhang, Shou-Kun,Liu, Ke,Ren, Baozeng,Gong, Jun-Fang,Niu, Jun-Long,Song, Mao-Ping
, p. 10399 - 10409 (2014)
Highly effective CuCl-mediated C-H alkoxylation of arenes and heteroarenes has been developed by using a 2-aminopyridine 1-oxide moiety as an N,O-bidentate directing group. The reaction proceeds smoothly using a broad range of substrates to afford o-alkox
Cobalt-catalyzed C(sp2)-H alkoxylation of aromatic and olefinic carboxamides
Zhang, Lin-Bao,Hao, Xin-Qi,Zhang, Shou-Kun,Liu, Zhan-Jiang,Zheng, Xin-Xiang,Gong, Jun-Fang,Niu, Jun-Long,Song, Mao-Ping
, p. 272 - 275 (2015)
The cobalt-catalyzed alkoxylation of C(sp2)-H bonds in aromatic and olefinic carboxamides has been developed. The reaction proceeded under mild conditions in the presence of Co(OAc)2?4H2O as the catalyst and tolerates a wide range of both alcohols and benzamide substrates, including even olefinic carboxamides. In addition, this reaction is the first example of the direct alkoxylation of alkenes through C-H bond activation.
One-Pot Direct Oxidation of Primary Amines to Carboxylic Acids through Tandem ortho-Naphthoquinone-Catalyzed and TBHP-Promoted Oxidation Sequence
Kim, Hun Young,Oh, Kyungsoo,Si, Tengda
supporting information, p. 18150 - 18155 (2021/12/09)
Biomimetic oxidation of primary amines to carboxylic acids has been developed where the copper-containing amine oxidase (CuAO)-like o-NQ-catalyzed aerobic oxidation was combined with the aldehyde dehydrogenase (ALDH)-like TBHP-mediated imine oxidation protocol. Notably, the current tandem oxidation strategy provides a new mechanistic insight into the imine intermediate and the seemingly simple TBHP-mediated oxidation pathways of imines. The developed metal-free amine oxidation protocol allows the use of molecular oxygen and TBHP, safe forms of oxidant that may appeal to the industrial application.
Process for preparing O-ethoxybenzoic acid chloride (by machine translation)
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, (2020/08/26)
The method comprises the following steps of (1) ethylation reaction, (2) alkali hydrolysis reaction and (3) acyl chlorination reaction, and is simple in reaction step, strong in operability, mild in reaction conditions, simple in process, easy to control, convenient to use and capable of easily controlling the byproduct HCl and CO. 2 The method is simple in process, convenient to operate, low in raw material cost, high in yield, good in quality and convenient for industrial production. (by machine translation)
O-ethoxy new synthetic process of formic acid
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Paragraph 0029; 0036-0040; 0041-0045; 0046-0050, (2019/04/04)
The invention belongs to the technical field of pharmaceutical intermediates, in particular to a O-ethoxy new synthetic process of formic acid. The alcohol into the reaction vessel, adding the solid KOH under stirring conditions, control the reaction temp
High diastereoselectivity in the yang photocyclization via remote hydrogen abstraction reaction
Jang, Mi,Park, Bong Ser
, p. 1509 - 1514 (2016/10/09)
1-Benzoyl-1-(o-alkoxyphenyl)cyclopropanes undergo Yang photocyclization to form dihydrobenzopyranols in a stereospecific manner. The cyclopropyl group at alpha position to carbonyls gives not only a bias in the most stable geometries of the starting ketones but also conformational restriction on geometries of biradical intermediates. More importantly, intramolecular hydrogen bonds seem to give an additional effect on conformational control of the biradical reactivity.
A 2-ethoxy carboxylic acid synthetic method of compound
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Paragraph 0020; 0022, (2017/03/24)
The invention discloses a synthesis method of a 2-ethoxybenzoic acid compound. The synthesis method comprises the following steps of orderly adding aromatic acylaminopyridine-1-oxide, cuprous chloride and an organic solvent into a reactor, stirring the mixture at a room temperature for 25-35min, adding potassium carbonate into the mixture after complex precipitates are produced, heating the reaction system to a temperature of 125-135 DEG C to cause a reaction lasting for 10-15h, after the reaction, carrying out extraction, drying, condensation and chromatographic separation to obtain an ethoxylated product, and carrying out alkaline hydrolysis and acidification to obtain the 2-ethoxybenzoic acid compound. The synthesis method has the advantages of easy acquisition of raw materials, cheap catalyst, mild reaction system, operation simpleness, high yield and substrate universality. The synthesis method has the yield of 87% and can realize guide base removal under mild conditions.
Synthesis and characterization of molecules containing thiazole and oxazole moieties and study of ESIPT phenomenon
Satam, Manjaree A.,Raut, Rajesh K.,Tathe, Abhinav B.,Sekar
, p. 1237 - 1248 (2013/01/15)
Two novel ESIPT molecules, 2-[4-(1,3-benzothiazol-2-yl)naphtho[1,2-d][1,3] oxazol-2-yl]phenol 9a and 4-[4-(1,3-benzothiazol-2-yl)naphtho[1,2-d][1,3]oxazol- 2-yl]benzene-1,3-diol 9b were synthesized by condensing 1-amino-3-(1,3- benzothiazol-2-yl)naphthale
Kinetics of proton transfer between ortho substituted benzoic acids and the carbinol base of crystal violet in toluene. Ortho effect on the reactivity of benzoic acids in apolar aprotic solvents
Sen Gupta, Susanta K.,Mishra, Sangeeta
experimental part, p. 4616 - 4623 (2011/06/26)
Apolar aprotic solvents are particularly advantageous for investigating the intrinsic ortho effect free from complications of specific solvent effects. A kinetic study for toluene-phase proton transfers between ortho F, Cl, Br, I, OMe, OEt, OPh, OAc, Me, NO2, COMe, COPh, OH, NH2, and H benzoic acids and crystal violet carbinol base has shown the forward rate constant (log k+1) is the most appropriate reactivity parameter in toluene. log k+1 (toluene) as compared to other reported reactivity parameters in benzene, toluene, or chlorobenzene has been found more sensitive to the ortho substituent effect. The regression results of the correlation of log k+1 (toluene) of the acids (except OH and NH2 substituted ones) according to seven ortho effect models are all very significant, and the best result is given by Fujita-Nishiokas model. The overall analysis reveals that a substituents ortho effect pattern is a 58:24:18 ratio of its ordinary electrical, proximity electrical, and steric effects and that the proximity electrical effect is the major component to account for the peculiarity of the substituents ortho effect. The results further favor the transmission of this effect mainly through the molecular cavity. The effect may, however, be outweighed by the steric component for bulky enough substituents, e.g., Me. The enhanced strength exhibited by salicylic acid in toluene has been quantitatively described using Pytela-Lisas δHB i parameter. The abnormally high log k+1 observed for anthranilic acid in toluene has been ascribed to a very extensive homoconjugation in its acid-acid anion complex induced by the acids three hydrogen bond donors.
Loss of benzene to generate an enolate anion by a site-specific double-hydrogen transfer during CID fragmentation of o-alkyl ethers of ortho-hydroxybenzoic acids
Attygalle, Athula B.,Bialecki, Jason B.,Nishshanka, Upul,Weisbecker, Carl S.,Ruzicka, Josef
experimental part, p. 1224 - 1234 (2009/09/29)
Collision-induced dissociation of anions derived from orffco- alkyloxybenzoic acids provides a facile way of producing gaseous enolate anions. The alkyloxyphenyl anion produced after an initial loss of CO2 undergoes elimination of a benzene molecule by a double-hydrogen transfer mechanism, unique to the ortho isomer, to form an enolate anion. Deuterium labeling studies confirmed that the two hydrogen atoms transferred in the benzene loss originate from positions 1 and 2 of the alkyl chain. An initial transfer of a hydrogen atom from the C-l position forms a phenyl anion and a carbonyl compound, both of which remain closely associated as an ion/neutral complex. The complex breaks either directly to give the phenyl anion by eliminating the neutral carbonyl compound, or to form an enolate anion by transferring a hydrogen atom from the C-2 position and eliminating a benzene molecule in the process. The pronounced primary kinetic isotope effect observed when a deuterium atom is transferred from the C-l position, compared to the weak effect seen for the transfer from the C-2 position, indicates that the first transfer is the rate determining step. Quantum mechanical calculations showed that the neutral loss of benzene is a thermodynamically favorable process. Under the conditions used, only the spectra from ortho isomers showed peaks at mlz 77 for the phenyl anion and mlz 93 for the phenoxyl anion, in addition to that for the ortho-specific enolate anion. Under high collision energy, the ortho isomers also produce a peak at mlz 137 for an alkene loss. The spectra of meta and para compounds show a peak at mlz 92 for the distonic anion produced by the homolysis of the O-C bond. Moreover, a small peak at mlz 136 for a distonic anion originating from an alkyl radical loss allows the differentiation of para compounds from meta isomers. Copyright
