Synthesis method of benzenetricarboxaldehyde compound

A technology of trimesicaldehyde and trimesicin is applied in the directions of oxidation to prepare carbonyl compounds, organic chemistry, etc., and achieves the effects of low synthesis cost, mild reaction conditions and simple operation.

Inactive Publication Date: 2013-09-04
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The technical problem to be solved by the present invention is to overcome the shortcomings of existing methods for synthesizing trimesic aldehydes, and provide a method for synthesizing trimesals with low cost, mild reaction conditions, simple operation and high product yield

Method used

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  • Synthesis method of benzenetricarboxaldehyde compound
  • Synthesis method of benzenetricarboxaldehyde compound
  • Synthesis method of benzenetricarboxaldehyde compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Taking the synthesis of 1,3,5-benzenetricarboxaldehyde as an example, its structural formula is as follows:

[0013]

[0014] Add 1.68g of 1,3,5-benzenetrimethanol and 0.32g of tetrabutylammonium bromide into a flask containing 100mL of dichloromethane, stir, and add 4.85g of potassium chromate into 150mL of aqueous sulfuric acid with a mass fraction of 30% , and then added dropwise to the flask, the molar ratio of 1,3,5-benzenetrimethanol to tetrabutylammonium bromide and potassium chromate was 1:0.1:2.5, and the reaction was carried out at room temperature for 2 hours. Wash with 10% sodium hydroxide aqueous solution and distilled water, wash until neutral, dry with anhydrous sodium sulfate, concentrate the solvent and separate by column chromatography to obtain white solid 1,3,5-benzenetricarbaldehyde, which is The yield is 97%, the melting point is 154-159°C, and the spectral data of the product are as follows:

[0015] 1 H NMR (300MHz, CDCl 3 ):δ=8.61(s,3H),10...

Embodiment 2

[0020] Taking the synthesis of 2,4,6-tribromo-1,3,5-benzenetricarbaldehyde as an example, its structural formula is as follows:

[0021]

[0022] In Example 1, the 1,3,5-benzenetrimethanol used was replaced with equimolar 2,4,6-tribromo-1,3,5-benzenetrimethanol, and other steps were the same as those in Example 1 to obtain White solid 2,4,6-tribromo-1,3,5-benzenetricarboxaldehyde, the yield is 89%, the melting point is >250°C, and the spectral data of the product are as follows:

[0023] 1 H NMR (300MHz, CDCl 3 ): δ=10.08(s, 3H).

[0024] 13 C NMR (75MHz, CDCl 3 ): δ=191.3, 134.2, 124.2.

[0025] IR(KBr)ν: 2887w, 1964w.

[0026] MS: theoretical value (C 9 H 3 Br 3 O 3 ) 395.7, the measured value is 395.7.

Embodiment 3

[0028] Taking the synthesis of 2,4,6-triethyl-1,3,5-benzenetricarbaldehyde as an example, its structural formula is as follows:

[0029]

[0030] In Example 1, the 1,3,5-benzenetrimethanol used was replaced with equimolar 2,4,6-triethyl-1,3,5-benzenetrimethanol, and other steps were the same as in Example 1, A white solid 2,4,6-triethyl-1,3,5-benzenetricarbaldehyde was obtained with a yield of 92%, and the spectral data of the product were as follows:

[0031] 1 H NMR (300MHz, CDCl 3 ): δ=10.58(s, 3H), 2.93(q, 6H), 1.22(t, 9H).

[0032] 13 C NMR (75MHz, CDCl 3 ): δ=194.5, 149.4, 134.6, 22.7, 16.7.

[0033] IR(KBr)ν: 2976w, 1696w, 1553w.

[0034] MS: Theoretical value C 15 H 18 O 3 (M+Na) ＋ 269.1, the measured value is 269.1.

[0035] The 2,4,6-triethyl-1,3,5-benzenetricarbinol in this example was synthesized according to the literature method, and the specific synthesis method was as follows: at 0 °C, 1.5g of 1,3,5-triethylbenzene was dissolved in In 35 mL of dr...

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Abstract

The invention discloses a synthesis method of a benzenetricarboxaldehyde compound. Benzenetrimethanol is oxidized to benzenetricarboxaldehyde in a phase transfer catalysis condition by using chromate or dichromate as an oxidant. Compared with the existing synthesis method, the synthesis method disclosed by the invention is mild in reaction conditions, simple to operate, low in synthesis cost, high in product yield and suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of having -CHO connected to carbon atoms of six-membered aromatic rings, in particular to a method for synthesizing trimesicaldehyde compounds. Background technique [0002] Tris-tricarboxaldehyde is an important intermediate in organic synthesis and can be used to synthesize various multi-armed dendrimers. For example, it can be reacted with ketones to synthesize chalcone compounds. Such compounds have great structural flexibility and can bind to different receptors, so they have a wide range of biological activities, such as anti-tumor, inhibition and scavenging of oxygen free radicals, anti-virus et al. (Bioorg. Med. Chem. Lett. 2003, 13, 1813-1815; Pharm. Res. 1998, 15, 39-46; Med. Chem. 2003, 46, 2813-2815). However, due to the existence of multiple aldehyde groups in trimesicaldehyde, it is difficult to synthesize it. Starting from the corresponding trivalent aryl alcohol, using an appropriate oxidan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/29C07C47/52C07C47/55
Inventor 魏俊发苏汉勇李璐常健张强任杏愉刘萍
Owner SHAANXI NORMAL UNIV
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