62-23-7Relevant articles and documents
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Wardner,Lowy
, p. 2510,2514 (1932)
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Studies on a dithiane-protected benzoin photolabile safety catch linker for solid-phase synthesis
Hong Boon Lee,Balasubramanian
, p. 3454 - 3460 (1999)
Substituted benzoinyl systems 8a-g, differing either in the substitution pattern, type of resin matrix used, or resin loading capacity, were prepared and the kinetics of their photolytic cleavage of Fmoc-β-alanine examined on resin. The linker systems 6a-g were assembled in near-quantitative yield using Corey-Seebach dithiane addition. The dithiane group that serves as a safety catch against premature photoreaction was removed by either oxidation or alkylation. Analytical methods that include FTIR and 13C gel-phase NMR spectroscopy were used for rapid reaction monitoring and sample characterization on resin. A survey of different substituted systems 8c-f for releasing Fmoc-β-alanine confirmed that the 3-alkoxybenzoin linker photocleaves most rapidly to give the highest yield (τ(1/2) = 6.7 min; 98% yield). Lowering the resin loading from 0.59 mmol/g in 8a to 0.26 mmol/g in 8b improved the cleavage kinetics to τ(1/2) = 2.6 min, 92% yield. Tentagel resin 8g exhibits similar photocleavage kinetics in both organic and aqueous media and when compared to the polystyrene counterpart, 8a. The 3- alkoxybenzoin linker 6a was also loaded with aryl carboxylic acids (12h,i) and hindered Fmoc-protected amino acids (12j-l) with varying degrees of success (57-100%) and dithiane deprotected (70-80%, 13h-1) followed by photocleavage with comparable efficiencies (8993% after 60 min).
Disproportionation of 4-Nitroacetophenone to 4-Aminoacetophenone and 4-Nitrobenzoic Acid
Wan, Peter,Xu, Xigen
, p. 4473 - 4474 (1989)
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2-(5-Arylterphenyl-4-yl)quinolines from 2-methylquinoline and 1-(het)aryl-3-phenylprop-2-yn-1-ones in just a one step: A miracle of molecular interplay
Trofimov, Boris A.,Belyaeva, Kseniya V.,Nikitina, Lina P.,Afonin, Andrei V.,Vashchenko, Alexander V.
, p. 267 - 269 (2018)
2-Methylquinoline reacts with 1-(het)aryl-3-phenylprop-2-yn-1-ones under mild transition metal-free conditions (55–60 °C, 20 mol% KOH, H2O, MeCN) to afford 2-{5’-(het)aryl[1,1’: 3’,1”]terphenyl-4’-yl}quinolines in up to 35% yield. The reaction likely proceeds via the intermediate 1,3-dipole followed by the double nucleophilic vinylation of the methyl group with two molecules of ynone and subsequent elimination of (het)arenecarboxylic acid.
Hey
, p. 2636,2638 (1932)
Use of ozone for preparing 4-nitrobenzoic acid in a closed process cycle
Galstyan,Tyupalo,Patapenko,Andreev
, p. 1777 - 1779 (2001)
The possibility of preparing 4-nitrobenzoic acid in a closed process cycle by oxidation of 4-nitrotoluene with an ozone air mixture was examined. The optimal conditions of oxidation with multiple use of mother liquors were found, and the conditions for crystallization of 4-nitrobenzoic acid from the reaction mixture were determined. The effects of water, acetic anhydride, and catalyst on the oxidation performed in mother liquors after filtration of the target product were examined.
Continuous production method of benzoic acid derivative
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Paragraph 0027; 0030-0031, (2021/11/14)
The invention relates to the technical field of preparation of benzoic acid derivatives. The invention particularly relates to a continuous production method of a benzoic acid derivative. The continuous reaction device is characterized by comprising a small-diameter sleeve, wherein the small-diameter sleeve is sleeved with a large-diameter sleeve, and a small pipeline is arranged between the small-diameter sleeve and the large-diameter sleeve, and a plurality of small holes are arranged on the small pipeline. The small-diameter casing is rotated, the large-diameter casing is fixed, and the reaction liquid composed of the nitric acid and the toluene derivative is between a small-diameter casing pipe and a large-diameter casing pipe.
Photo-induced deep aerobic oxidation of alkyl aromatics
Wang, Chang-Cheng,Zhang, Guo-Xiang,Zuo, Zhi-Wei,Zeng, Rong,Zhai, Dan-Dan,Liu, Feng,Shi, Zhang-Jie
, p. 1487 - 1492 (2021/07/10)
Oxidation is a major chemical process to produce oxygenated chemicals in both nature and the chemical industry. Presently, the industrial manufacture of benzoic acids and benzene polycarboxylic acids (BPCAs) is mainly based on the deep oxidation of polyalkyl benzene, which is somewhat suffering from environmental and economical disadvantage due to the formation of ozone-depleting MeBr and corrosion hazards of production equipment. In this report, photo-induced deep aerobic oxidation of (poly)alkyl benzene to benzene (poly)carboxylic acids was developed. CeCl3 was proved to be an efficient HAT (hydrogen atom transfer) catalyst in the presence of alcohol as both hydrogen and electron shuttle. Dioxygen (O2) was found as a sole terminal oxidant. In most cases, pure products were easily isolated by simple filtration, implying large-scale implementation advantages. The reaction provides an ideal protocol to produce valuable fine chemicals from naturally abundant petroleum feedstocks. [Figure not available: see fulltext.].
