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Aromatic aldehyde synthesis method

A synthesis method and technology for aromatic aldehydes, which are applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of high reaction pressure and harsh conditions, and achieve easy yield, easy product and fast reaction rate. Effect

Active Publication Date: 2019-05-31
SHANGHAI BILOR NEW MATERIALS TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, the conditions of the hydroformylation reaction involving syngas are relatively harsh, for example, a high reaction pressure is usually required, so special pressurization equipment is required, and CO and H 2 are dangerous gases

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  • Aromatic aldehyde synthesis method
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preparation example Construction

[0046] In a preferred embodiment, in order to increase the reaction rate, the above synthesis method further includes the step of adding a free radical initiator.

[0047] In a further preferred embodiment, the free radical initiator is tert-butyl peroxybenzoate.

[0048] According to a preferred embodiment of the second aspect of the present invention, a synthetic method of aromatic aldehyde has the following synthetic route:

[0049]

[0050] Wherein, X is I or Br;

[0051] The synthetic method comprises the following steps:

[0052] Add halogenated aromatic hydrocarbon B, glyoxylic acid, palladium acetate, n-butyl bis(1-adamantyl) phosphine, organic base and polar aprotic solvent into the reaction vessel, heat the reaction, and post-treatment to obtain the aromatic aldehyde γ .

[0053] In a preferred embodiment, in order to increase the reaction rate, the above synthesis method further includes the step of adding a free radical initiator.

[0054] In a further prefe...

Embodiment 1

[0061] Catalytic Synthesis of Benzaldehyde and Cinnamaldehyde

[0062]

[0063] Add iodobenzene (1.02g, 5mmol), palladium acetate (56.12mg, 0.25mmol), triphenylphosphine (262.3mg, 1mmol), DMF 5ml, glyoxylic acid (1.85g, 25mmol), triethylamine to the flask (2.77g, 27.5mmol), tert-butyl peroxybenzoate (48.5mg, 0.25mmol), sealed, heated at 110°C, and reacted for 3 hours. Cool to room temperature, add 150ml of water, extract with dichloromethane 3×100ml, combine the organic phases, wash once with saturated sodium chloride solution, dry over anhydrous sodium sulfate, evaporate the organic solvent under reduced pressure, and purify by column chromatography (the mobile phase is ethyl acetate Esters: petroleum ether = 20:1). 159 mg of benzaldehyde was obtained, with a yield of 30%, and 218 mg of cinnamaldehyde, with a yield of 33%.

[0064] Wherein, the product is characterized as follows:

[0065] Benzaldehyde: 1 H NMR (400MHz, CDCl 3 )δ9.95(s,1H),7.44-7.82(m,5H);

[0066] C...

Embodiment 2

[0068] Catalytic Synthesis of p-methoxybenzaldehyde and p-methoxycinnamaldehyde

[0069]

[0070] Add p-methoxyiodobenzene (1.17g, 5mmol), palladium acetate (56.12mg, 0.25mmol), triphenylphosphine (262.3mg, 1mmol), DMF 5ml, glyoxylic acid (1.85g, 25mmol) into the flask , DBU (4.18g, 27.5mmol), tert-butyl peroxybenzoate (48.5mg, 0.25mmol), sealed, heated at 110°C, and reacted for 3 hours. Cool to room temperature, add 150ml of water, extract with dichloromethane 3×10ml, wash the organic phase once with saturated sodium chloride solution, dry over anhydrous sodium sulfate, evaporate the organic solvent to dryness under reduced pressure, and purify by column chromatography (mobile phase is ethyl acetate: Petroleum ether=15:1). 149.6 mg of p-methoxybenzaldehyde was obtained, with a yield of 22%, and 89 mg of p-methoxycinnamaldehyde, with a yield of 11%.

[0071] Wherein, the product is characterized as follows:

[0072] p-Methoxybenzaldehyde: 1 H NMR (400MHz, CDCl 3 )δ9.89...

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Abstract

The invention provides an aromatic aldehyde synthesis method. Aryl halide serves as a starting material, glyoxylic acid serves as a carbonyl source, proper palladium catalysts and phosphine-containingorganic ligands are used, and aromatic aldehyde serving as a target product is prepared by heating and sealing reaction. Raw materials of the synthesis method are easily obtained, operation is simple, the product is easily separated, total reaction rate is high, process cost is low, and the yield of the target product is easily adjusted. Therefore, the aromatic aldehyde synthesis method is beneficial to large-scale industrial production of the aromatic aldehyde.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing aromatic aldehydes. Background technique [0002] As we all know, aromatic aldehydes are widely used in medicine, dyes, pesticides, spices and other fields. In addition, aromatic aldehydes are also effective intermediates in the synthesis of fine chemicals. For many years, the synthesis method of aromatic aldehydes is mainly based on the formylation of aromatic compounds, but there are generally disadvantages such as low yield, serious equipment corrosion, and complicated process. In actual industrial production, with the increasing demand for aromatic aldehydes, people are trying to find a new production process. [0003] With the development of transition metal catalysis, catalytic formylation has become an important method for the preparation of aldehydes. In the past few decades, under the catalysis of transition metals such as Ru, Rh, a...

Claims

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Application Information

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IPC IPC(8): C07D209/08C07C67/313C07C69/76C07C45/00C07C47/575C07C47/54C07C47/232C07C47/277
Inventor 沈颖
Owner SHANGHAI BILOR NEW MATERIALS TECH
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