Method for synthesizing aryl acetate derivative under catalysis of surface modified sludge charcoal

A technology for aryl acetate and surface modification, which is applied in the preparation of organic compounds, chemical instruments and methods, and preparation of carboxylate esters. It can solve the problems that have not been reported in relevant literature, and achieve easy separation and purification and simple preparation. , to achieve the effect of reuse

Active Publication Date: 2019-10-25
NANJING NORMAL UNIVERSITY
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Problems solved by technology

At present, surface-modified sludge charcoal is used as a catalyst to realize the construction of C-C bonds through the arylation reaction of diazonium ester compounds and aryl boronic acid compounds. There is no relevant information about the one-step reaction to generate aryl acetate derivatives. It is reported in the literature that it is very innovative and provides a new idea for the selection of catalysts in organic synthesis

Method used

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  • Method for synthesizing aryl acetate derivative under catalysis of surface modified sludge charcoal
  • Method for synthesizing aryl acetate derivative under catalysis of surface modified sludge charcoal
  • Method for synthesizing aryl acetate derivative under catalysis of surface modified sludge charcoal

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preparation example Construction

[0039] Preparation of sludge charcoal: domestic sewage sludge from Dalian sewage treatment plant, China, dried in a muffle furnace at 80-200°C to constant weight (optimum temperature 105°C), and heated at a flow rate of 200-1000mL / min Heating to 400-800°C (optimum temperature 600°C) under pure nitrogen (optimum flow rate 500mL / min) and heating rate 1-10°C / min (optimum heating rate 3°C / min), continuous carbonization 2 -8h (the best carbonization time is 4h), when the temperature in the furnace drops to room temperature, sludge carbon (SW) can be obtained.

[0040] Preparation of surface modified sludge charcoal: soak sludge charcoal in the modifier for 24 hours, wash with deionized water until the pH of the washing solution reaches 3-7, then recover the solid and dry it at room temperature to obtain Surface modified sludge charcoal.

[0041] Wherein, the modifying agent is HClO 4 (concentration: 10-70wt%, optimum concentration: 35.4wt%), HCl (concentration: 10-50wt%, optimum ...

Embodiment 1

[0044]

[0045] At room temperature, successively weigh ethyl phenyldiazoacetate 1a (0.5mmol), phenylboronic acid 2a (0.8mmol), SW-I (50mg) in a 25mL Schlenk reaction tube, and add 1, 5mL of 2-dichloroethane, stirred at room temperature for 0.5h, moved to a 70°C oil bath with magnetic stirring heater, and reacted for 6 hours. TLC detected that the raw materials had reacted completely, stopped the reaction, cooled the reaction solution to room temperature, and filtered it with suction , the filter cake was washed with dichloromethane until the filtrate was colorless, concentrated under reduced pressure to remove volatile components, and separated by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=10: 1), the target product 3a (61 mg, yield 51%) was obtained in a colorless, transparent and viscous form, and the target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0046] Embodiment 2 (comparative example: different catalyst contrasts)

[0047]

[0048] At room temperature, successively weigh ethyl phenyldiazoacetate 1a (0.5mmol), phenylboronic acid 2a (0.8mmol), SW-Ⅴ (50mg) in a 25mL Schlenk reaction tube, add 1, 5mL of 2-dichloroethane, stirred at room temperature for 0.5h, moved to an oil bath magnetic stirring heater at 70°C to react for 6 hours, TLC detected that the raw materials were not completely reacted (contrast experiment, ensure the same reaction time), stop the reaction, Cool the reaction solution to room temperature, filter with suction, wash the filter cake with dichloromethane until the filtrate is colorless, concentrate under reduced pressure to remove volatile components, and separate by silica gel column chromatography (eluent: petroleum ether (60-90°C) / acetic acid Ethyl ester, v / v=10:1), the target product 3a (37 mg, yield 31%) was obtained as colorless, transparent and viscous, and the target product was confirme...

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Abstract

The invention discloses a method for synthesizing an aryl acetate derivative under the catalysis of surface modified sludge charcoal. According to the method, the construction of a C-C bond is realized by an arylation reaction realized by taking the surface modified sludge charcoal as a catalyst and a diazoester compound and an arylboronic acid compound as starting raw materials, and thus, the aryl acetate derivative is generated. According to the method, the sludge charcoal prepared from residual sludge generated after urban sewage treatment is adopted as the catalyst, and therefore, the method is wide in source, simple in preparation, low in cost, green and environment-friendly; and the aryl acetate derivative is available in reaction raw materials, mild in conditions, high in yield andcapable of realizing gram-scale reaction and has an industrialization prospect. Meanwhile, the recycle of wastes is realized, the problem of urban sludge is difficult to treat is relieved, and the purpose of green chemistry is realized.

Description

technical field [0001] The invention relates to a method for catalytically synthesizing aryl acetate derivatives by using surface modified sludge charcoal. Background technique [0002] With the continuous development of my country's economy, people's living standards have been greatly improved, but with it comes serious pollution (water pollution, air pollution, noise pollution), water pollution is particularly prominent, and water pollution is closely related to urban sewage Related, the unreasonable discharge of urban sewage is an important cause of water pollution. In recent decades, my country has invested heavily in the construction of a large number of sewage treatment facilities in large and medium-sized cities. Although the urban pollution problem has been gradually alleviated, the treatment and disposal of the resulting large amount of sludge has not been well resolved in China. a question of . Sludge is an accompanying organism in the sewage treatment process, mos...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/65C07C69/738C07C69/616B01J21/18B01J27/06B01J35/10
CPCC07C67/343B01J21/18B01J27/06B01J35/61C07C69/65C07C69/738C07C69/616Y02P20/584
Inventor 黄菲张志朋丁天行徐军于杨戴传超梅艳珍乔纳森·贝尔
Owner NANJING NORMAL UNIVERSITY
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