Preparation method of 2-(chloromethyl)-5,6-dimethoxy-3-methyl-1,4-para benzoquinone

A technology of trimethoxytoluene and dimethoxy, which is applied in the preparation of quinone oxide, organic chemistry, etc., can solve the problems of limited industrial application value, harsh reaction conditions, and difficulty in obtaining it. The method is simple and practical, the reaction operation is simple, low cost effect

Inactive Publication Date: 2012-11-14
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction conditions of this synthetic route are harsh, the reagent lithium aluminum hydride used is flammable and explosive, expensive and difficult to ob

Method used

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  • Preparation method of 2-(chloromethyl)-5,6-dimethoxy-3-methyl-1,4-para benzoquinone
  • Preparation method of 2-(chloromethyl)-5,6-dimethoxy-3-methyl-1,4-para benzoquinone
  • Preparation method of 2-(chloromethyl)-5,6-dimethoxy-3-methyl-1,4-para benzoquinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: The preparation method of 2-chloromethyl-5,6-dimethoxy-3-methyl-1,4-p-benzoquinone, the specific operation is as follows:

[0029] (1) Weigh 9.1g (0.05mol) of 3,4,5-trimethoxytoluene and dissolve it in 6.5ml N,N-dimethylformamide (0.09mol). Under nitrogen protection, control the reaction temperature at 0°C. Then 9.2g (0.06mol) of phosphorus oxychloride was slowly added dropwise, and the drop was completed after 1 hour, then the temperature was raised to 60°C for 10 hours, and the reaction was stopped. The reaction solution was poured into 200g of crushed ice and stirred for reaction. The mass percentage concentration is 30% sodium hydroxide solution to neutralize to neutral, a large amount of solids are precipitated, and compound 2 is obtained by filtration, which is a light yellow solid, melting point: 59-60 ° C, yield: 97%. 1 HNMR (500MHz, CDCl 3 ): 10.28 (s, 1H, -CHO), 3.86-3.73 (t, 9H, -OCH 3 ), 2.44(s,3H, -CH 3 );

[0030] (2) Weigh 3.2g (0.015mol) o...

Embodiment 2

[0034] Example 2: The preparation method of 2-chloromethyl-5,6-dimethoxy-3-methyl-1,4-p-benzoquinone, the specific operation is as follows:

[0035] (1) Weigh 9.1g (0.05mol) of 3,4,5-trimethoxybenzene and dissolve it in 4.5ml N,N-dimethylformamide (0.06mol). Under the protection of nitrogen, control the reaction temperature at 5°C and slowly Add 9.20 g (0.06 mol) of phosphorus oxychloride dropwise, and drop it for about 1.5 hours, then raise the temperature to 80°C and react for 7 hours, stop the reaction, pour the reaction solution into 150 g of crushed ice and stir the reaction, and finally the solution is mixed with 30% The sodium hydroxide solution was neutralized to neutral, a large amount of solids were precipitated, and compound 2 was obtained by filtration as a light yellow solid; melting point: 59-60°C, yield: 98%. 1 HNMR (500MHz, CDCl 3 ): 10.28 (s, 1H, -CHO), 3.86-3.73 (t, 9H, -OCH 3 ), 2.44(s,3H, -CH 3 );

[0036] (2) Weigh 3.2g (0.015mol) of compound 2 and 1.2...

Embodiment 3

[0040] Example 3: The preparation method of 2-chloromethyl-5,6-dimethoxy-3-methyl-1,4-p-benzoquinone, the specific operation is as follows:

[0041] (1) Weigh 9.1g (0.05mol) of 3,4,5-trimethoxybenzene and dissolve it in 7.5ml N,N-dimethylformamide (0.1mol). Under nitrogen protection, control the reaction temperature at 3°C , then slowly drop phosphorus oxychloride 15.2g (0.10mol), drop after 2 hours, then heat up to 100 ° C for 4 hours, stop the reaction, pour the reaction solution into 300g of crushed ice and stir the reaction, and finally the solution Neutralize to neutral with 30% sodium hydroxide solution, a large amount of solids are precipitated, and compound 2 is obtained by filtration as a light yellow solid, melting point: 59-60°C, yield: 95%. 1 HNMR (500MHz, CDCl 3 ): 10.28 (s, 1H, -CHO), 3.86-3.73 (t, 9H, -OCH 3 ), 2.44(s,3H, -CH 3 );

[0042] (2) Weigh 3.2g (0.015mol) of compound 2 and 2.25g (0.075mol) of paraformaldehyde, mix them, and add dropwise 27.0ml of h...

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Abstract

The invention discloses a preparation method of 2-(chloromethyl)-5,6-dimethoxy-3-methyl-1,4-para benzoquinone, wherein the 2-(chloromethyl)-5,6-dimethoxy-3-methyl-1,4-para benzoquinone is the key intermediate for preparation of coenzyme Q compounds. The preparation method comprises the steps of using 3,4,5-trimethoxytoluene as raw material, and carrying out four steps of Vilsmeier-Haack reaction, Blanc chloromethylation reaction, Dakin reaction and oxidation reaction to obtain 2-(chloromethyl)-5,6-dimethoxy-3-methyl-1,4-para benzoquinone with high purity. The overall yield is up to more than 50%. The method provided by the invention has the advantages of rich source of raw material, high yield, good quality and purity of the product, simple process, low cost and wide application prospect.

Description

technical field [0001] The invention relates to a preparation method of 2-chloromethyl-5,6-dimethoxy-3-methyl-1,4-p-benzoquinone, a key intermediate for preparing coenzyme Q compounds, and belongs to the field of organic synthesis. Background technique [0002] Coenzyme Q is a kind of fat-soluble substance that naturally exists on the cell membrane of all eukaryotes. It participates in the energy conversion process related to biological oxidation as a key electron transporter in the mitochondrial respiratory chain of cells. Antioxidative protection of molecules such as proteins, enzymes, membrane phospholipids, DNA / RNA, etc. Further studies in recent years have shown that coenzyme Q compounds also have the functions of regulating cell growth, metabolism, differentiation, energy distribution, regulating body immunity, and improving the function of vascular endothelial system (Turunen M, Olsson J, Dallner G . Metabolism and function of coenzyme Q. Biochimica et Biophysica Ac...

Claims

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Application Information

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IPC IPC(8): C07C50/28C07C46/06
Inventor 杨健王金杨波
Owner KUNMING UNIV OF SCI & TECH
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