A method for efficiently synthesizing 1,3-bis(4-hydroxyphenyl)-2-propen-1-one

A technology for hydroxyphenyl and p-hydroxyacetophenone, applied in the field of efficient synthesis of 1,3-di-2-propen-1-one, which can solve the problems of complex time-consuming, long reaction time, and low yield , to achieve the effect of solving low yield, ensuring activity and simple operation

Active Publication Date: 2021-12-14
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, achieving efficient and rapid synthesis of this compound has been challenging
[0003] The traditional method uses p-hydroxybenzaldehyde and p-hydroxyacetophenone as raw materials, uses inorganic strong acid or strong base as catalyst, and reacts in ethanol-water mixed solution. Side reactions such as Cannizzaro disproportionation and Michael addition
[0004] Document (T.Narender, et al., Tetrahedron Letters, 2007,48,3177) has reported the reaction that takes boron trifluoride as catalyst, yet, according to the method in document, repeated test, productive rate is very low (<20% ) and there are many raw materials that do not participate in the reaction; and subsequent steps such as liquid separation, washing, drying, and column chromatography separation are required, which are complicated and time-consuming

Method used

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  • A method for efficiently synthesizing 1,3-bis(4-hydroxyphenyl)-2-propen-1-one
  • A method for efficiently synthesizing 1,3-bis(4-hydroxyphenyl)-2-propen-1-one
  • A method for efficiently synthesizing 1,3-bis(4-hydroxyphenyl)-2-propen-1-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 1.22g (10mmol) p-hydroxybenzaldehyde, 1.77g (13mmol) p-hydroxyacetophenone, 6g 4A type molecular sieve into the round bottom flask, add 10mL 1,4-dioxane, stir to dissolve the reactant Add 0.25 mL of boron trifluoride ether; dissolve 1 mL of boron trifluoride ether in 4 mL of dioxane, and inhale it into a syringe without a rubber tip; fix the syringe on the syringe pump and adjust the appropriate rate so that trifluoride Boronium ether solution was injected into the substrate solution within 5 hours at the same time, while stirring and heating to 80°C for reaction, after the injection was completed, the reaction was continued for 10 hours, cooled to room temperature, and then the product solution was added dropwise to 400mL deionized water, The wine-red powder precipitate was obtained by suction filtration, and the pure product was obtained by vacuum drying at 80° C. for 10 h, with a yield of 98%.

Embodiment 2

[0027] 1.46g (12mmol) p-hydroxybenzaldehyde, 1.36g (10mmol) p-hydroxyacetophenone, 6g anhydrous MgSO 4 Put it into a round bottom flask, add 5mL of methanol, stir to dissolve the reactant, then add 0.3mL of boron trifluoride ether; dissolve 0.8mL of boron trifluoride ether in 2.2mL of ethanol, and seal it well. The boron trifluoride ether solution was added dropwise to the substrate solution within 3 hours at the same time, and started to stir and heat to 80°C to react at the same time. After the injection was completed, the reaction was continued for 5 hours and cooled to room temperature, and then the product solution was added dropwise to 300mL Suction filter in deionized water to obtain a wine red powder precipitate, and vacuum dry at 80°C for 10 hours to obtain a pure product with a yield of 99%.

Embodiment 3

[0029] 1.22g (10mmol) p-hydroxybenzaldehyde, 1.36g (10mmol) p-hydroxyacetophenone, 6g anhydrous NaSO 4 Put it into a round bottom flask, add 5mL of ethanol, stir to dissolve the reactant, then add 0.2mL of boron trifluoride ether; dissolve 1.5mL of boron trifluoride ether in 8.8mL of ethanol, and use a dropping funnel to make the The boron ether solution was added dropwise to the substrate solution at the same time within 2 hours. While adding, stir and heat to 60°C for reaction. After the injection, continue to react for 5 hours and cool down to room temperature, then add the product solution dropwise into 500mL deionized water , suction filtration to obtain a wine red powder precipitate, and vacuum drying at 80°C for 10 hours to obtain a pure product with a yield of 96%.

[0030] 1H NMR (400Hz, DMSO-d6): 10.0 (s, 1H), 10.3 (s, 1H), 8.1 (d, 2H), 7.64-7.72 (m, 4H), 6.8-6.9 (m, 4H).

[0031] FTIR: 1650cm -1 It is -C=O stretching vibration absorption peak, 1601cm -1 It is -C=...

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Abstract

The invention discloses a method for efficiently synthesizing 1,3-bis(4-hydroxyphenyl)-2-propene-1-one, which belongs to the field of organic chemical synthesis. The method is through the Claisen-Schmidt reaction, with p-hydroxybenzaldehyde and p-hydroxyacetophenone as reactants, and boron trifluoride ether as a catalyst, by gradually adding the catalyst to the raw material solution, and adding dry Agents can effectively ensure the activity of the catalyst, thereby optimizing the reaction to obtain the product. After the reaction, the product solution was added dropwise into deionized water, and the precipitate was collected and dried. This method is convenient and quick, easy to implement, can realize the synthesis of 1,5-bis(4-hydroxyphenyl)-1,4-pentadien-3-one with high yield (>98%), and has important practical application value , suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for efficiently synthesizing 1,3-bis(4-hydroxyphenyl)-2-propen-1-one. Background technique [0002] 1,3-bis(4-hydroxyphenyl)-2-propen-1-one is a chalcone derivative containing phenolic hydroxyl group, which has anti-cancer, anti-bacterial, anti-convulsant, anti-HIV, anti-hyperglycemic, anti- Anti-inflammatory, anti-aging, anti-bacterial, anti-oxidation, anti-plasmodium, anti-tuberculosis, anti-virus, anti-ulcer and other biological activities have important applications in medicine. In addition, the large conjugated π bonds contained in it make it photoactive, and it can be used as a raw material for the synthesis of photocurable resins, and is an important organic chemical synthesis intermediate. However, achieving efficient and rapid synthesis of this compound has been challenging. [0003] The traditional method uses p-hydroxybenzaldehyde and p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/74C07C49/835
CPCC07C45/74C07C49/835
Inventor 王涛宗润发
Owner NANCHANG UNIV
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