Synthesis method of aryl aldehyde compound

A synthesis method and compound technology, which is applied in the field of synthesis of aryl aldehyde compounds, can solve the problems of waste treatment, inconvenient production and application, etc., and achieve the effects of low cost, mild reaction conditions and high reaction yield

Active Publication Date: 2020-04-07
HUAIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of waste salts and transition metal catalysts produced by stoichiometric oxidants often brings waste disposal problems, which is inconvenient for practical production and application

Method used

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  • Synthesis method of aryl aldehyde compound
  • Synthesis method of aryl aldehyde compound
  • Synthesis method of aryl aldehyde compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The preparation method of aryl aldehyde compounds, the steps are as follows:

[0047] Add photocatalyst 4CzIPN (0.1mol%), DBU (10mol%), solvent acetonitrile 1.5mL, 4-methoxyphenylacetic acid (0.2mmol) into the 25mL reaction tube, stir in the air at room temperature 25℃, under blue light irradiation After 4 hours of reaction, the final product was separated by silica gel column chromatography, and the yield of the final product was 90% based on the molar amount of aryl acetic acid as 100%.

[0048] The specific results are as follows:

[0049]

[0050] 1 H NMR (400MHz, Chloroform-d) δ 9.87 (s, 1H), 7.83 (d, J = 8.8 Hz, 2H), 6.99 (d, J = 8.8 Hz, 2H), 3.87 (s, 3H). 13 C NMR (101 MHz, Chloroform-d) δ 190.80, 164.60, 131.96, 129.93, 114.31, 55.56.

Embodiment 2

[0052] The preparation method of aryl aldehyde compounds, the steps are as follows:

[0053] Add photocatalyst 4CzIPN (0.1mol%), DBU (10mol%), solvent acetonitrile 1.5mL, 3-methoxyphenylacetic acid (0.2mmol) into the 25mL reaction tube, stir in the air at room temperature 25℃, under blue light irradiation After 8 hours of reaction, the final product was separated by silica gel column chromatography. The yield of the final product was 85% based on the molar amount of aryl acetic acid as 100%.

[0054] The specific results are as follows:

[0055]

[0056] 1 H NMR (400MHz, Chloroform-d) δ9.98 (s, 1H), 7.51 - 7.42 (m, 2H), 7.43 - 7.37 (m, 1H), 7.18 (m, 1H), 3.86 (s, 3H). 13 C NMR (101 MHz, Chloroform-d) δ 192.15, 160.16, 137.82, 130.04, 123.55, 121.53, 112.06, 55.48.

Embodiment 3

[0058] The preparation method of aryl aldehyde compounds, the steps are as follows:

[0059] Add photocatalyst 4CzIPN (0.1mol%), DBU (10mol%), solvent acetonitrile 1.5mL, 2-methoxyphenylacetic acid (0.2mmol) into the 25mL reaction tube, stir in the air at room temperature 25℃, under blue light irradiation After 8 hours of reaction, the final product was separated by silica gel column chromatography, and the yield of the final product was 86% based on the molar amount of aryl acetic acid as 100%.

[0060] The specific results are as follows:

[0061]

[0062] 1 H NMR (400MHz, Chloroform-d) δ 10.46 (s, 1H), 7.81 (dd, J = 7.9, 1.8 Hz, 1H), 7.54 (m, 1H), 7.08–6.95 (m, 2H), 3.91 ( s, 3H). 13 C NMR (101MHz, Chloroform-d) δ189.78, 161.83, 135.98, 128.44, 124.79, 120.62, 111.66, 55.61.

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Abstract

The invention discloses a synthesis method of an aryl aldehyde compound. The method comprises the following step: carrying out an oxidative decarboxylation reaction on an aryl acetic acid compound andan organic alkali under the catalytic action of a visible light catalyst to obtain the aryl aldehyde compound. According to the method, the aryl aldehyde compound is generated through one-step oxidative decarboxylation of aryl acetic acid at room temperature under visible light in an open system, so that the method is simple to operate, mild in reaction condition, cheap and easily available in raw materials and catalysts and high in reaction yield, and is an environment-friendly synthesis method.

Description

Technical field [0001] The invention relates to a method for synthesizing aryl aldehyde compounds, in particular to a method for realizing one-step synthesis of aryl aldehyde compounds from aryl acetic acid compounds by photocatalysis under room temperature conditions, and belongs to the technical field of organic synthesis. Background technique [0002] Aryl aldehyde compounds are widely present in natural products, drugs and material molecules. Because of the unique reaction properties of aldehyde groups, they have a wide range of important applications in many fields such as organic synthesis, drug synthesis, and material chemistry. Generally, aryl aldehyde compounds can be prepared by heating the oxidative decarboxylation of aryl acetic acid in the presence of transition metal catalysis or equivalent strong oxidants (J.Org.Chem.2014,79,1867-1871, Chin. J. Chem., 2009, 27, 1007-1011, Tetrahedron Lett. 2017, 58, 2822-2825), these synthesis methods usually require the addition o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/54C07C47/575C07C47/542C07C47/55
CPCC07C45/54C07C47/575C07C47/542C07C47/55Y02P20/584
Inventor 唐莉莉朱甜
Owner HUAIHUA UNIV
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