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Method for preparing 2,3,4,5-tetramethoxytoluene

A technology of tetramethoxytoluene and trimethoxytoluene, applied in the field of preparation of 2,3,4,5-tetramethoxytoluene, which can solve the problem of unsynthesized routes and process research, harsh reaction conditions, and inability to apply production, etc. problem, to achieve the effect of complete environmental friendliness, reduction of reaction steps, and reduction of product production cost

Inactive Publication Date: 2011-01-12
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 2,3,4,5-Tetramethoxytoluene was first proposed by Syper L et al. ), they used pyrogallic acid as raw material to carry out 2,3,4,5- The synthesis of tetramethoxytoluene, but this method has a long synthetic route, the price of the reagents used is also special, and the reaction conditions of the multi-step reaction are harsh, so it cannot be applied to production and has only scientific research value
In addition, Eren Doron etc. have also proposed that 2,3,4,5-tetramethoxytoluene can be prepared by using 3,4,5-trimethoxytoluene as a raw material through a two-step reaction of bromination and methoxy substitution, but None of them studied the synthetic route and process

Method used

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  • Method for preparing 2,3,4,5-tetramethoxytoluene
  • Method for preparing 2,3,4,5-tetramethoxytoluene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] 1) Preparation of Compound 3: Weigh 18.2g (0.10mol) of raw material 3,4,5-trimethoxytoluene and place it in a 250ml three-necked flask, add 100ml of acetic acid and stir to dissolve, add NaBr11.0g (0.11mol), then Add 30% H dropwise at room temperature 2 o 2 About 50ml, react for 3-4 hours; add 150ml of water to the reaction solution, then extract with petroleum ether (80ml×2), combine the organic phases, wash once with water, dry over anhydrous sodium sulfate, filter, evaporate the petroleum ether under reduced pressure to obtain the product It is nearly 26.0 g of colorless oil, and the yield of crude product is nearly 100%. 1 HNMR: δ 6.58(s, 1H), δ 3.86(s, 3H), δ 3.83(s, 3H), δ 3.81(s, 3H), δ 2.33(s, 3H). MS(z / e): 260 .

[0019] The crude compound 3 was directly used in the next reaction without purification by distillation.

[0020] 2) Preparation of Compound 1: Weigh 26.0g (0.10mol) of Compound 3 in a 500ml dry three-necked flask, N 2 Add 6.2g (0.20mol) of sodiu...

Embodiment 2

[0022] Preparation of Compound 3: Weigh 18.2g (0.10mol) of raw material 3,4,5-trimethoxytoluene and place it in a 250ml three-necked flask, add a mixed solvent of 10ml acetic acid and 90ml tetrahydrofuran and stir to dissolve, add NaBr11.0g (0.11 mol), and then dropwise added 30% H at room temperature 2 o 2 About 40ml, react for 3-4 hours; add 150ml of water to the reaction solution, then extract with petroleum ether (80ml×2), combine the organic phases, wash once with water, dry over anhydrous sodium sulfate, filter, evaporate the petroleum ether under reduced pressure to obtain the product It is a colorless oil, and the yield is basically the same as in the above examples.

[0023] The preparation of compound 1: take by weighing 26.0g (0.10mol) compound 3 and place in 500ml dry three-necked flask, N 2 Add 6.2g (0.20mol) of sodium methoxide and 10ml of methanol under protection, stir well, then add 1.0g of CuBr and 5.0ml of DMF, heat the reaction mixture to 110-120°C for 3-...

Embodiment 3

[0025] Preparation of Compound 3: Weigh 18.2g (0.10mol) of raw material 3,4,5-trimethoxytoluene and place it in a 250ml three-necked flask, add a mixed solvent of 10ml formic acid and 90ml methanol and stir to dissolve, add NaBr11.0g (0.11 mol), then slowly add 50ml of an aqueous solution containing 30.0g (0.11mol) of potassium persulfate at 45°C, and react for 7-8 hours; add 150ml of water to the reaction solution, then extract with petroleum ether (80ml×2), and combine The organic phase was washed once with water, dried over anhydrous sodium sulfate, filtered, and the petroleum ether was distilled off under reduced pressure to obtain the product as a colorless oil. Yield is basically the same as above embodiment.

[0026] The preparation of compound 1 is the same as the above-mentioned examples.

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Abstract

The invention discloses a method for preparing 2, 3, 4, 5-isoimerubrine toluene. The method uses 3, 4, 5-trimethoxy toluene as a raw material to prepare the high-quality 2, 3, 4, 5-isoimerubrine toluene through two steps of bromic reaction and methoxyl group displacement reaction, wherein a bromination reagent in the method adopts a mixture of sodium bromide, potassium bromide or lithium bromide and hydrogen peroxide or other suitable oxidants; and the methoxyl group displacement reaction is performed only by using CuCl or other cuprous salts as a catalyst, and DMF as an auxiliary catalyst atnormal pressure. The method avoids rigorous reaction conditions of using costly reagents and poisonous reagents, pressurizing and the like, and gets good effect, has total reaction yield normally above 90 percent and less reaction steps; besides, the used reagent is easily available, the production cost of products is further reduced, and the method is completely environment-friendly.

Description

technical field [0001] The invention relates to a method for preparing the synthetically important intermediate 2,3,4,5-tetramethoxytoluene of cardiovascular drug coenzyme Q. Background technique [0002] Coenzyme Q is a commonly used clinical drug for treating cardiovascular diseases, and it can also be used as an important component of nutritional health products (Zhang Jizhong et al. Journal of Shanghai Institute of Applied Technology, 2004, 4(4): 301-305). There are generally three sources of its application, namely animal tissue and organ extraction, microbial fermentation and chemical semi-synthesis. Since the chemical synthesis method has the advantages of saving food, good product quality, and low production cost, companies at home and abroad have begun to use chemical semi-synthesis for mass production of coenzyme Q. Among them, 2,3,4,5-tetramethoxytoluene is an important intermediate for chemical semi-synthesis of coenzyme Q. [0003] 2,3,4,5-Tetramethoxytoluene ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/205C07C41/01
Inventor 杨健杨波吴远双
Owner KUNMING UNIV OF SCI & TECH
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