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Method for synthesizing alpha-chloro-cinnamyl aldehyde compound

A compound, the technology of chlorinated meat, which is applied in the field of preparation of α-chlorocinnamaldehyde compounds, can solve the problems of complex catalysts, difficult synthesis, expensive starting materials, etc., and achieve high yield, simple operation, common substrates adaptable effect

Inactive Publication Date: 2018-01-30
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the catalyst of the first method is too complex; the starting material of the second method is expensive and difficult to synthesize; the ligand of the last method is complex

Method used

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  • Method for synthesizing alpha-chloro-cinnamyl aldehyde compound
  • Method for synthesizing alpha-chloro-cinnamyl aldehyde compound
  • Method for synthesizing alpha-chloro-cinnamyl aldehyde compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] Add 0.3mmol of o-phenylcinnamaldehyde and 0.45mmol of ferric chloride into a 15mL pressure-resistant tube, and then add 3mL of acetonitrile / water (V:V=100:1) as a solvent. Next, magnetically stir at 140° C. for 12 h. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate=40:1 as an eluent). The substance was a yellow solid, the chemical name was o-phenyl-α-chlorocinnamaldehyde, and the yield was 69%.

[0026] Characterization data: 1 H NMR (CDCl 3 ,500MHz):9.35(s,1H),8.26(d,J=8.0Hz,1H),7.56-7.43(m,7H),7.34-7.33(m,2H); 13 C NMR (CDCl 3 ,125MHz): δ186.5, 145.4, 143.7, 139.6, 132.9, 130.8, 130.3, 130.3, 130.2, 129.8, 129.7, 128.1, 127.3.

Embodiment 2

[0028]

[0029] Add 0.3mmol of o-phenylcinnamaldehyde and 0.9mmol of copper chloride into a 15mL pressure-resistant tube, and then add 3mL of dimethyl sulfoxide as a solvent. Then, magnetic stirring was performed at 150° C. for 8 h. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate=40:1 as an eluent). The substance was a yellow solid, the chemical name was o-phenyl-α-chlorocinnamaldehyde, and the yield was 61%.

[0030] Characterization data: 1 H NMR (CDCl 3 ,500MHz):9.35(s,1H),8.26(d,J=8.0Hz,1H),7.56-7.43(m,7H),7.34-7.33(m,2H); 13 C NMR (CDCl 3 ,125MHz): δ186.5, 145.4, 143.7, 139.6, 132.9, 130.8, 130.3, 130.3, 130.2, 129.8, 129.7, 128.1, 127.3.

Embodiment 3

[0032]

[0033] Add 0.3 mmol of o-phenylcinnamaldehyde and 0.3 mmol of cuprous chloride into a 15 mL pressure-resistant tube, and then add 3 mL of acetonitrile / water (V:V=400:1) as a solvent. Then, magnetically stir at 90° C. for 24 h. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate=40:1 as an eluent). The substance was a yellow solid, the chemical name was o-phenyl-α-chlorocinnamaldehyde, and the yield was 44%.

[0034] Characterization data: 1 H NMR (CDCl 3 ,500MHz):9.35(s,1H),8.26(d,J=8.0Hz,1H),7.56-7.43(m,7H),7.34-7.33(m,2H); 13 C NMR (CDCl 3 ,125MHz): δ186.5, 145.4, 143.7, 139.6, 132.9, 130.8, 130.3, 130.3, 130.2, 129.8, 129.7, 128.1, 127.3.

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Abstract

The invention relates to a method for synthesizing an alpha-chloro-cinnamyl aldehyde compound. The method comprises the steps of adding a cinnamyl aldehyde compound represented by a formula a shown inthe description into a chloride containing organic solvent, carrying out a full reaction at the temperature of 90 DEG C to 150 DEG C, and subjecting a reaction solution to separation and purificationafter the reaction is completed, thereby obtaining the alpha-chloro-cinnamyl aldehyde compound represented by a formula b, wherein the batch-fed substance quantity ratio of the chloride to the cinnamyl aldehyde compound is (1 to 3): 1; and R in the formula a and R in the formula b are the same and are methyl, methoxy, phenyl or C1-C4alkyl phenyl, the quantity of substituents is n, and n is 1 or 2. Compared with the prior art, the method has the advantages that the chloride is cheap and readily available and is relatively low in toxicity, no waste water and waste acid is produced during the reaction, environmental pollution is not caused, no complicated and expensive ligand is required to be used, the yield is high, the substrate universality is high, and the operation is simple and convenient.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for preparing α-chlorocinnamaldehyde compounds. Background technique [0002] α-Chlorocinnamaldehyde compounds are an important class of organic compounds, useful intermediates in organic synthesis, and important monomers in polymer synthesis. They are widely used in the pharmaceutical industry and are very important pharmaceutical intermediates. The chlorination of olefins reported in the literature mainly includes the following methods: (1) decarboxylation of carboxylic acids under heating conditions (see Journal of Dispersion Science and Technology, 2007, 28, 613-616); (2) conversion of metal salts (see Journal of Organometallic Chemistry, 2009, 694, 592-597); (3) conversion method of halogenated olefins (see Organic Letters, 2016, 18, 1904). But the catalyst of the first method is too complex; the starting material of the second method is expensive and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/63C07C47/24C07C49/235
Inventor 刘运奎张海峰鲍汉扬
Owner ZHEJIANG UNIV OF TECH
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