Method for preparing cinnamyl aldehyde compounds

A compound, the technology of cinnamaldehyde, which is applied in the field of preparation of cinnamaldehyde compounds, can solve the problems of pretreatment and preparation of catalysts, and achieve the effects of easy separation, high yield, and cheap and easy-to-obtain raw materials

Inactive Publication Date: 2015-12-09
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these two methods avoid the use of precious metal catalysts, they also have disadvantages such as the need for a dry environment and the need for pretreatment of the catalyst.

Method used

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  • Method for preparing cinnamyl aldehyde compounds
  • Method for preparing cinnamyl aldehyde compounds

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0021] Synthesis of Cinnamaldehyde

[0022] Add 0.2mmol 1-phenyl-2-propyn-1-ol, 0.30mmol 50wt% phosphorous acid aqueous solution, and 0.5mL dichloromethane into the reactor. Under nitrogen atmosphere, heat to 110°C, keep stirring for 2h, stop the reaction, cool to room temperature, add saturated sodium carbonate solution to wash, extract with dichloromethane, dry, distill off the solvent under reduced pressure, and separate the crude product by column chromatography to obtain Target product, yield 91%. 1 HNMR (400MHz, CDCl 3 ):δ9.70(d,J=7.7Hz,1H),7.57-7.55(m,2H),7.49-7.42(m,4H),6.72(dd,J=16.0,7.7Hz,1H). 13 CNMR (100MHz, CDCl 3 ): δ193.6, 152.7, 133.9, 131.2, 129.0, 128.5, 128.4.

Synthetic example 2

[0024] Synthesis of p-fluorocinnamaldehyde

[0025] Add 0.2mmol of 1-p-fluorophenyl-2-propyn-1-ol, 0.30mmol of 50wt% phosphorous acid aqueous solution, and 0.5mL of dichloromethane into the reactor. Under nitrogen atmosphere, heat to 110°C, keep stirring for 2h, stop the reaction, cool to room temperature, add saturated sodium carbonate solution to wash, extract with dichloromethane, dry, distill off the solvent under reduced pressure, and separate the crude product by column chromatography to obtain Target product, yield 88%. 1 HNMR (400MHz, CDCl 3 ): δ9.69(d, J=7.6Hz, 1H), 7.59-7.54(m, 2H), 7.44(d, J=16.0Hz, 1H), 7.15-7.09(m, 2H), 6.65(dd, J=16.0,7.6Hz,1H). 13 CNMR (100MHz, CDCl 3 ):δ193.4,165.42(d,J C-F =253.2Hz), 151.3, 130.4(d, J C-F =8.7Hz), 130.2(d, J C-F =3.4Hz), 128.3(d, J C-F =2.3Hz), 116.3(d, J C-F =22.1Hz).

Synthetic example 3

[0027] Synthesis of p-chlorocinnamaldehyde

[0028]Add 0.2mmol of 1-p-chlorophenyl-2-propyn-1-ol, 0.30mmol of 50wt% phosphorous acid aqueous solution, and 0.5mL of dichloromethane into the reactor. Under nitrogen atmosphere, heat to 110°C, keep stirring for 2h, stop the reaction, cool to room temperature, add saturated sodium carbonate solution to wash, extract with dichloromethane, dry, distill off the solvent under reduced pressure, and separate the crude product by column chromatography to obtain Target product, yield 85%. 1 HNMR (400MHz, CDCl 3 ):δ9.70(d,J=7.6Hz,1H),7.50(d,J=8.5Hz,2H),7.45-7.40(m,3H),6.69(dd,J=16.0,7.6Hz,1H) . 13 CNMR (100MHz, CDCl 3 ): δ193.3, 151.0, 137.2, 132.4, 129.6, 129.4, 128.9.

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Abstract

The invention provides a method for preparing cinnamyl aldehyde compounds. According to the method, under the nitrogen condition, propargyl alcohol is adopted as a raw material, a phosphorous acid aqueous solution is adopted as a medium, and the cinnamyl aldehyde compounds are synthesized in organic solvents. According to the method, the easily-obtained raw material and the cheap phosphorous acid aqueous solution are adopted, a reaction is conducted under the nitrogen condition, no ligand or peroxide or valuable catalyst or microwave radiation or other special reaction conditions are adopted, the reaction condition is simple, the product is high in selectivity and productivity, and good industrial application prospects are achieved.

Description

【Technical field】 [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of cinnamaldehyde compounds. 【Background technique】 [0002] Cinnamaldehyde compounds are important raw materials and intermediates in organic synthesis. The aldehyde group is easily converted into other useful functional group compounds, such as cyano group, carboxylic acid, hydroxyl group and amide. Cinnamaldehyde compounds have many unique properties, and have very important application value in the fields of flavors and fragrances, daily chemicals, medicine and food additives. For example, o-hydroxycinnamaldehyde has various activities such as antibacterial, anti-inflammatory, and inhibition of cancer cell proliferation, and has shown a good effect on the treatment of lung cancer; p-chlorocinnamaldehyde has antibacterial and growth-promoting effects, and can be used as a feed additive. Cinnamaldehyde compounds not only have excellent biological activit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/06C07C47/232C07C47/24C07C47/277C07C45/26C07C45/51C07C211/48C07C209/68
Inventor 周永波刘立鑫董建玉李中文尹双凤韩立彪
Owner HUNAN UNIV
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