- Synthesis method of 4,4'-diphenyl ether dicarboxylic acid
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The invention discloses a 4,4'-diphenyl ether dicarboxylic acid synthesis method, which comprises: S1, carrying out a dehydration reaction on p-hydroxybenzoate, an alkali and a solvent at a temperature of 110-120 DEG C for 2-4 h under a protection gas to obtain a mixed solution; S2, adding a catalyst and p-halo benzoate into the mixed solution obtained in the step S1, carrying out a heating coupling reaction at a reaction temperature of 145-195 DEG C, adding a solvent after the reaction is finished, and performing extraction, liquid separation and crystallization to obtain a solid 4,4'-diphenyl ether dicarboxylic acid diester; and S3, carrying out heating hydrolyzing on the 4,4'-diphenyl ether dicarboxylic acid diester obtained in the step S2 in an aqueous alkali solution and a solvent, adding an acid to adjust the pH value to be acidic, and carrying out crystallization and filtration to obtain the 4,4'-diphenyl ether dicarboxylic acid. The method is simple in process operation, low inequipment requirement, high in product purity, less in three wastes generated in the production process, environment-friendly and high in industrial feasibility, and the total yield of the two-step reaction can reach more than 80%.
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Paragraph 0033; 0035-0037
(2020/05/01)
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- Palladium-Catalyzed Formal Cross-Coupling of Diaryl Ethers with Amines: Slicing the 4-O-5 Linkage in Lignin Models
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Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value-added platform chemicals instead of using fossil-based resources. Lignins are aromatic polymers linked by three types of ether bonds (α-O-4, β-O-4, and 4-O-5 linkages) and other C?C bonds. Among the ether bonds, the bond dissociation energy of the 4-O-5 linkage is the highest and the most challenging to cleave. To date, 4-O-5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross-coupling of diaryl ether 4-O-5 linkage models with amines is reported, in which dual C(Ar)?O bond cleavages form valuable nitrogen-containing derivatives.
- Zeng, Huiying,Cao, Dawei,Qiu, Zihang,Li, Chao-Jun
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supporting information
p. 3752 - 3757
(2018/03/13)
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- Visible-light induced oxidative Csp3-H activation of methyl aromatics to methyl esters
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Direct functionalization of readily available hydrocarbons under mild conditions fulfills the requirements of green and sustainable chemistry. In this work, a mild and green catalytic oxidative Csp3-H activation of methyl aromatics using O2via photocatalysis has been achieved. A lot of methyl aromatics can be tolerated, providing a green route for aromatic methyl carboxylates. In addition, this protocol can be performed on a gram scale.
- Zhang, Lingling,Yi, Hong,Wang, Jue,Lei, Aiwen
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supporting information
p. 5122 - 5126
(2016/10/05)
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- Synthesis of 10,10-Dioxo-10λ6-Phenoxathiin Derivatives by Reaction of 4,4′-Oxydibenzoic Acid with Sulfur-Containing Electrophiles
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A method for the synthesis of 4-substituted derivatives of 10,10-dioxo-10λ6-phenoxathiin-2,8-dicarboxylic acid by the reaction of 4,4′-oxydibenzoic acid with strong sulfur-containing electrophiles was developed. The interaction with chlorosulfonic acid or oleum was shown to produce a phenoxathiin ring by initial substitution of hydrogen at positions 2 and 2′ followed by intramolecular cyclization to 4-chlorosulfonyl(sulfo)-10,10-dioxo-10λ6-phenoxathiin-2,8-dicarboxylic acid. Using an analogous approach, methods for the synthesis of 4-nitro- and 4,6-dinitro-10,10-dioxo-10λ6-phenoxathiin-2,8-di-carboxylic acids were developed.
- Yashchenko,Pap,Kalechits,Makey,Ol'khovik
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p. 1470 - 1476
(2015/02/19)
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- Direct aerobic photo-oxidative syntheses of aromatic methyl esters from methyl aromatics using anthraquinone-2,3-dicarboxylic acid as organophotocatalyst
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This paper reports a useful method for facile direct syntheses of aromatic methyl esters from methyl aromatics by aerobic photo-oxidation using anthraquinone-2,3-dicarboxylic acid as an organophotocatalyst.
- Tada, Norihiro,Ikebata, Yuki,Nobuta, Tomoya,Hirashima, Shin-Ichi,Miura, Tsuyoshi,Itoh, Akichika
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experimental part
p. 616 - 619
(2012/07/13)
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- Preparation process of 4,4'-Dicarboxydiphenyl ethers or derivatives thereof
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4,4'-Dicarboxydiphenyl ether can be prepared by reacting diphenyl ether with an acetylating agent in the presence of a transition metal salt of trifluoromethane-sulfonic acid and an alkali metal perhalogenate to obtain 4,4'-diacetyldiphenyl ether and oxidizing the 4,4'-diacetyldiphenyl ether with an alkali metal hypohalogenite. A 4,4'-dicarboxydiphenyl ether, which is represented by the following formula (2): wherein Zs each represents -OH, -OR, -NH2, -NHR or -NR2, each R being an alkyl group having a carbon number not greater than 4, or a derivative thereof can be prepared by reacting a 4,4'-dihalodiphenyl ether, which is represented by the following formula (1): wherein X represents a halogen element, with carbon monoxide, a base and a nucleophile in the presence of a palladium catalyst and a bidentate phosphine compound.
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- Synthesis and antitumour activity of new derivatives of flavone-8-acetic acid (FAA). Part 4: Variation of the basic structure
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A range of 11 derivatives of flavone-8-acetic acid (FAA) in which the structure has been substantially altered in different ways have been prepared and their anti-tumour activity evaluated in vitro against a panel of human and murine tumour cell lines and in vivo against MAC 15A. The generally poor activity observed shows that the basic structure cannot be altered much without destroying the activity.
- Alan Aitken,Bibby, Michael C.,Cooper, Patricia A.,Double, John A.,Laws, Andrea L.,Ritchie, Robert B.,Wilson, David W.J.
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p. 181 - 188
(2007/10/03)
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- Palladium-catalyzed reactions of bisarenediazoniutn salts: Two-fold Heck reaction, carbonylation and cross-coupling regimen
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Two-fold Heck reaction, carbonylation and cross-coupling reactions of bisarenediazonium salts have been carried out in high yields under mild, aqueous alcoholic conditions to provide a new synthetic repertoire for tetraaryls and other aromatic derivatives having extended conjugation.
- Sengupta, Saumitra,Sadhukhan, Subir Kumar,Bhattacharyya, Sanchita,Guha, Joydeep
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p. 407 - 410
(2007/10/03)
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- THERMOLYSE DES CARBONATES D'ARYLE INITIEE PAR LES BASES : I-MECANISME PAR SNAR DANS LE CAS DES CARBONATES D'ARYLE PORTEURS DE GROUPES ELECTRO-ATTRACTEURS IDENTIQUES.
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The base-initiated thermolysis of diaryl carbonates leads to diaryl ethers.Kinetics evidences (Ea= 26 kcal.mole-1 )are given, showing that reaction proceeds via SNAr mechanism.Phenoxide is recognised as the active species.
- Jost, Philippe,Forestiere, Alain,Sillion, Bernard,Le Perchec, Pierre
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p. 4311 - 4314
(2007/10/02)
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