A kind of method of one-pot synthetic diaryl ketal

A synthesis method and dimethoxy technology, which are applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as not meeting the requirements of green manufacturing, and achieve short steps, good practicability, and simple post-processing. Effect

Active Publication Date: 2020-12-15
SOUTHEAST UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Wherein, the synthesis of acid chloride needs to use acid chloride reagents such as oxalyl chloride, thionyl chloride, and Friedel-Crafts acylation often uses excessive aluminum trichloride as catalyst, and the use of these materials can be accompanied by a large amount of waste acid gas ( Hydrogen chloride gas, carbon dioxide, sulfur dioxide, etc.) and waste water (strongly acidic, containing aluminum trichloride), which is a big problem for industrial scale-up production, does not meet the needs of green manufacturing

Method used

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  • A kind of method of one-pot synthetic diaryl ketal
  • A kind of method of one-pot synthetic diaryl ketal
  • A kind of method of one-pot synthetic diaryl ketal

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Embodiment one: the synthesis of 1-(dimethoxy-phenyl-methyl)-4-methoxy-benzene

[0025]

[0026] 250mL four-necked flask with magnetic stirring, thermometer and reflux condenser, successively added trifluoroacetic anhydride (42.0g, 200mmol), anisole (13.0g, 120mmol), boron trifluoride etherate complex (1.42g, 10mmol ), benzoic acid (12.2 g, 100 mmol) was added in portions, and the temperature was raised to 30-40° C. for 6 hours under stirring to obtain a dark brown solution. Cool down to room temperature, add methanol (60mL) and trimethyl orthoformate (31.8g, 300mmol), the color of the solution turns light red, heat up to 55-60°C for 18h, and add triethylamine (2.0g) after cooling down The pH was adjusted to alkaline, and the color of the solution further became pale yellow. Concentrate under reduced pressure to remove most of the solvent, and a solid precipitates. Add heptane (50mL) to make a slurry, filter, and air-dry at 40°C to obtain white 1-(dimethoxy-phenyl-m...

Embodiment 2

[0027] Embodiment two: the synthesis of 1-(dimethoxy-phenyl-methyl)-4-isopropyl-benzene

[0028]

[0029] 250mL four-necked flask with magnetic stirring, thermometer and reflux condenser, successively added trifluoroacetic anhydride (42.0g, 200mmol), cumene (14.4g, 120mmol), boron trifluoride diethyl ether complex (1.42g, 10mmol ), benzoic acid (12.2g, 100mmol) was added in portions, and the temperature was raised to 30-40° C. for 4 hours under stirring to obtain a wine-red solution. Cool down to room temperature, add methanol (60mL) and trimethyl orthoformate (31.8g, 300mmol), the color becomes light yellow, heat up to 55-60°C for 18h, add triethylamine (2.0g) to adjust the temperature pH to alkaline, the color of the solution further becomes lighter. Concentrate under reduced pressure to remove most of the solvent, add dichloromethane (60mL) to dissolve, wash twice with water (30mL*2), collect the organic layer, concentrate under reduced pressure to obtain an oily substa...

Embodiment 3

[0030] Embodiment three: the synthesis of 2-chloro-5-[dimethoxy-(4-methoxy-phenyl)-methyl]-thiophene

[0031]

[0032] 250mL four-necked flask with magnetic stirring, thermometer and reflux condenser, successively added trifluoroacetic anhydride (42.0g, 200mmol), anisole (16.2g, 150mmol), boron trifluoride diethyl ether complex (2.13g, 15mmol ), 5-chloro-2-thiophenecarboxylic acid (16.3 g, 100 mmol) was added in portions, and the temperature was raised to 30-40° C. for 5 hours under stirring to obtain a deep reddish-brown solution. Cool down to room temperature, add methanol (60 mL) and trimethyl orthoformate (31.8 g, 300 mmol), the color change is not obvious. Reheat to 55-60°C and keep it warm for 24 hours. After cooling down, add triethylamine (3.0 g) to adjust the pH to alkaline, concentrate most of the solvent to obtain a reddish-brown oil, add dichloromethane (80 mL) to dissolve, and water ( 40mL*2) washed twice, collected the organic layer, concentrated under reduce...

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Abstract

The invention discloses a one-pot method used for synthesis of diaryl methyl ketal. The on-pot method is shorter in process, and is more effective. A novel synthesis strategy is provided for synthesisof some complex diaryl ketones. According to the one-pot method, an aryl carboxylic acid and a R-substituted benzene compound are selected, in the presence of trifluoroactic anhydride, boron trifluoride diethyl etherate is taken as a catalyst, direct acylation reaction is carried out, without treatment, methanol and trimethyl orthoformate are added for continuous reaction so as to obtain a diarylmethyl ketal product, so that one-pot synthesis of diaryl methyl ketal from aromatic acids is realized.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a method for synthesizing diaryl ketal in one pot. Background technique [0002] Diaryl ketones are a class of compounds that directly connect two aromatic groups with a carbonyl group, and have the following general formula: [0003] [0004] Among them, Ar1 and Ar2 respectively represent aromatic groups. Since this type of compound contains two aromatic groups and is conjugated with a carbonyl group, it can be used as an important material in organic electroluminescent devices. The characteristics of aggregation and good film-forming properties, and the rigid groups in the molecule can also improve the thermal stability of the material, which has a wide range of applications. In the field of medicine, diaryl ketones can be used as important raw materials to be converted into medicinal compounds. For example, the raw materials of several leptinoid diab...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/50C07C43/315C07C43/307C07D333/28
CPCC07C41/50C07D333/28C07C43/315C07C43/307
Inventor 胡林邹平左智伟刘文博邱小龙苟少华魏万国李小跃袁希萌
Owner SOUTHEAST UNIV
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