Synthesis method of 9,10-anthracenedicarboxylic acid

A technology for the synthesis of anthracene dicarboxylic acid, applied in chemical instruments and methods, preparation of carboxylate salts, preparation of organic compounds, etc., capable of solving the problems of cumbersome synthesis routes and low yields

Pending Publication Date: 2021-09-14
YULIN NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the existing methods, the synthesis of 9,10-anthracene dicarboxyl

Method used

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  • Synthesis method of 9,10-anthracenedicarboxylic acid
  • Synthesis method of 9,10-anthracenedicarboxylic acid
  • Synthesis method of 9,10-anthracenedicarboxylic acid

Examples

Experimental program
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Embodiment 1

[0025] (1) Add 1.00 g, 0.6 mmol of anthracene in a 100 mL round bottom flask, then add 20 mL of 48% hydrogen bromide in aqueous solution, then add 5 mL of acetic acid solution, slowly add 1.0 g, 12.8 mmol of paraformaldehyde and 0.04g, 0.128mmol N,N,N-trimethyl-1-tetradecylammonium bromide, heated to 45~55℃ and heated under N 2 React under protection for 24 to 48 hours. After the reaction is completed, cool to room temperature to produce a large amount of solids, filter and wash the filter residue with water and ethanol, and dry to obtain the first intermediate;

[0026] (2) Add 1.99g, 5.5mmol of the first intermediate to a 100mL round bottom flask, then add 20mL of dry dimethyl sulfoxide (DMSO) and stir to dissolve, accurately measure 20mL of sodium ethoxide solution and 2mL of 2-nitropropane The mixed solution was slowly added dropwise into a round-bottomed flask in a constant pressure dropping funnel, and reacted at room temperature for 24 to 36 hours. After the reaction, t...

Embodiment 2

[0034] The difference between the present embodiment and Example 1 is: in step (1), the mol ratio of paraformaldehyde and N,N,N-trimethyl-1-tetradecyl ammonium bromide is 95:1; step ( In 2), the eluent in the chromatography column is PE:EA=95:1; in step (3), the molar ratio of sulfamic acid and sodium chlorite is 1:1.2.

Embodiment 3

[0036] The difference between the present embodiment and embodiment 1 is: in step (1), the mol ratio of paraformaldehyde and N,N,N-trimethyl-1-tetradecyl ammonium bromide is 105:1; In step (2), the eluent in the chromatography column is PE:EA=105:1.

[0037] The second intermediate 9,10-dialdehyde group anthracene prepared in Example 1 is an orange solid with a yield of 60%, such as figure 1 , figure 2 as shown, 1 H NMR nuclear magnetic resonance analysis results are 1 H NMR (500MHz, DMSO) δ11.46(s, 2H), 8.81(dd, J=6.9, 3.3Hz, 4H), 7.78(dd, J=6.9, 3.2Hz, 4H). 13 C NMR nuclear magnetic resonance analysis results are 13 C NMR (126 MHz, DMSO) δ 196.7, 132.2, 129.9, 128.8, 124.9.

[0038] The 9,10-anthracene dicarboxylic acid prepared in Example 1 is an orange solid with a yield of 60%, as shown in image 3 , Figure 4 , Figure 5 as shown, 1 H NMR nuclear magnetic resonance analysis results are 1 H NMR (500MHz, DMSO) δ 14.16 (s, 2H), 8.07 (dd, J=6.7, 3.2Hz, 4H), 7.69 (...

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Abstract

The invention relates to an anthracene compound, and in particular, relates to a synthesis method of 9,10-anthracenedicarboxylic acid, wherein the synthesis method comprises the steps: dissolving anthracene in a hydrogen bromide solution and an acetic acid solution, then adding trioxymethylene and N,N,N-trimethyl-1-tetradecyl ammonium bromide, and reacting under the protection of N2 to obtain a first intermediate; then dissolving the first intermediate in dimethyl sulfoxide, dropwise adding a mixed solution of a sodium ethoxide solution and 2-nitropropane, filtering, and performing chromatographic separation to obtain a second intermediate; and adding a mixed solvent, sulfamic acid and sodium chlorite into the second intermediate to react, adding an ammonium chloride solution after the reaction is finished, and then extracting, drying and filtering to obtain a 9,10-anthracenedicarboxylic acid solid. The method can accurately position the ninth and tenth positions of anthracene, and has the advantages of strong positioning effect, few reaction byproducts, easy separation of target products, and high yield.

Description

technical field [0001] The present invention relates to a synthesis method of anthracene compound, more specifically, it relates to a synthesis method of 9,10-anthracene dicarboxylic acid. Background technique [0002] Anthracene, also called scintillation crystal, the centers of the three rings of anthracene are on a straight line, and anthracene is a colorless flaky crystal; the chemical activity of the 9 and 10 positions in the anthracene molecule is relatively high. [0003] 9,10-Anthracene dicarboxylic acid is a fused ring aromatic acid, which is a common organic ligand. Among the existing synthetic methods, the method of using n-butyllithium is the most mature method, which mainly uses anthracene as raw material, and through bromine Synthesis of bromoanthracene, and reaction with carbon dioxide under the catalysis of butyllithium to obtain the target product 9,10-anthracene dicarboxylic acid. However, in the existing methods, the synthesis of 9,10-anthracenedicarboxyl...

Claims

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Application Information

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IPC IPC(8): C07C51/29C07C63/46
CPCC07C51/29C07C45/42C07C17/263C07C63/46C07C47/546C07C22/04
Inventor 黄国保陶萍芳陈志林陈珊刘敏黎莹成俊英林韦梁元栊郑冰雲黄冰玥陈文煊孙杨杨
Owner YULIN NORMAL UNIVERSITY
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