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Synthesizing method of multi-aryl substituted naphthol derivate

The technology of a naphthol derivative and a synthesis method is applied in the synthesis field of polyaryl-substituted naphthol derivatives, and achieves the effects of simple operation, high reaction yield and good optical activity

Inactive Publication Date: 2017-11-24
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In summary, there have been no reports on the synthesis of polyaryl-substituted naphthols and anthracenols from phenolic compounds. Therefore, the present invention draws on the work of predecessors, and proceeds from the carbon-hydrogen bond activation reaction to design and study The preparation of multi-substituted naphthol compounds by the reaction of phenol derivatives and toluene has good application value

Method used

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  • Synthesizing method of multi-aryl substituted naphthol derivate
  • Synthesizing method of multi-aryl substituted naphthol derivate
  • Synthesizing method of multi-aryl substituted naphthol derivate

Examples

Experimental program
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Effect test

Embodiment 1

[0034] (1) starting from phenol to synthesize dimethylcarbamoyl-protected phenol derivatives, as shown in the following formula:

[0035]

[0036] The specific process is as follows: add 0.94g, 10mmol phenol and 30mL acetonitrile in turn to a 100mL round bottom flask with a magnet, start stirring on the stirrer to completely dissolve the phenol, and then add 2.74g, 20mmol carbonic acid to the reaction system Potassium, fully stirred for 20min, then slowly added dropwise 1.6g, 15mmol of dimethylcarbamoyl chloride from the constant pressure dropping funnel, continued to stir for 2 hours after the dropwise addition, and judged whether the reaction was complete by thin-layer chromatography, the reaction was complete Finally, stop stirring, filter first, then spin dry the filtrate by rotary evaporator, then add 50mL dichloromethane and 20mL water to the system for extraction, combine the organic phases, dry with anhydrous sodium sulfate for 30min, and spin dry to obtain the crude...

Embodiment 2

[0042] (1) starting from m-cresol to synthesize the m-cresol derivative of dimethylcarbamoyl protection, as shown in the following formula:

[0043]

[0044]The specific reaction process is: add 1.08g, 10mmol m-cresol and 30mL acetonitrile successively to a 100mL round bottom flask with a magnet, start stirring on the stirrer to completely dissolve the phenol, and then add 2.74g , 20mmol of potassium carbonate, fully stirred for 20min, then slowly added 1.6g, 15mmol of dimethylcarbamoyl chloride dropwise from the constant pressure dropping funnel, and continued to stir for 2 hours after the dropwise addition, and judged whether the reaction was complete by thin-layer chromatography , after the reaction is complete, stop stirring, filter first, then spin dry the filtrate through a rotary evaporator, then add 50mL dichloromethane and 20mL water to the system for extraction, combine the organic phases, dry with anhydrous sodium sulfate for 30min, and spin dry. The crude produc...

Embodiment 3

[0051] (1) starting from m-chlorophenol to synthesize the m-chlorophenol derivative of dimethylcarbamoyl protection, as shown in the following formula:

[0052]

[0053] Concrete reaction process is: add 1.28g, 10mmol m-chlorophenol and 30mL acetonitrile successively in the 100mL round-bottomed flask that has magneton, start to stir on stirrer, make phenol dissolve completely, then add 2.74g in reaction system, 20mmol of potassium carbonate, fully stirred for 20min, then slowly added dropwise 1.6g, 15mmol of dimethylcarbamoyl chloride from the constant pressure dropping funnel, continued to stir for 2 hours after the addition was completed, and judged whether the reaction was complete by thin-layer chromatography. After the reaction is complete, stop stirring, first filter, then spin the filtrate to dryness with a rotary evaporator, then add 50 mL of dichloromethane and 20 mL of water to the system for extraction, combine the organic phases, dry with anhydrous sodium sulfate...

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Abstract

The invention discloses a synthesizing method of a multi-aryl substituted naphthol derivate. The method comprises the following steps: performing cyclization reaction on a phenol derivate and a diaromatic acetylene derivate in an organic solvent under the effects of a rhodium catalyst, a silver additive and an oxidizing agent; then processing after the reaction is finished to obtain the multi-aryl substituted naphthol derivate. The synthesizing method is simple to operate; the multi-aryl substituted naphthol derivate can be obtained by one step, so that the reaction yield is high.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing polyaryl-substituted naphthol derivatives. Background technique [0002] Polyaryl-substituted naphthol derivatives are a class of compounds with a higher conjugated system, and the synthesis of such compounds has the following advantages: (1) its good electrical conductivity can be used in the preparation and development of organic photoelectric materials; ( 2) By modifying the hydroxyl group, various functional groups can be introduced into the molecule, thereby adjusting the photoelectric properties of the molecule. However, the synthesis method of such molecules has not been reported yet. [0003] In recent years, the research on transition metal-catalyzed carbon-hydrogen bond activation has achieved rapid development. Compared with traditional coupling reactions, this method has the following advantages: (1) The raw materials are cheap and easy to o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/06C07C271/44C07C269/00
CPCC07C269/00C07C269/06C07C271/44
Inventor 齐陈泽冯若昆高远
Owner SHAOXING UNIVERSITY