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Preparation method of 1, 3, 5-trimethoxybenzene

A technology of trimethoxybenzene and methanol, which is applied in ether preparation, ester reaction preparation of ether, organic chemistry, etc., can solve the problems of cumbersome operation, high preparation cost, and low purity, and achieve high yield and purity, and stable product quality , good reproducibility

Active Publication Date: 2021-03-23
NANJING CORE TECH CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, the methods for preparing 1,3,5-trimethoxybenzene include: phloroglucinol methylation method, trihaloanisole etherification method, etc., in the trihaloanisole etherification method, etc., However, these methods often have disadvantages such as cumbersome operation, difficult acquisition of raw materials, high preparation cost, low yield, and low purity.
As Chinese patent (CN1491927A) just disclosed 1,3,5-tribromobenzene reacts with sodium methylate under the catalysis of cuprous iodide to prepare trimethylphloroglucinol, but the post-treatment of this process is more loaded down with trivial details, obtains The quality of trimethylphloroglucinol is average and cannot meet the needs of pharmaceutical grades

Method used

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  • Preparation method of 1, 3, 5-trimethoxybenzene
  • Preparation method of 1, 3, 5-trimethoxybenzene
  • Preparation method of 1, 3, 5-trimethoxybenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of crude 1,3,5-trimethoxybenzene

[0044] Add 150 mL of N,N-dimethylamide to the compound 1,3,5-tribromobenzene (100.0 g, 0.32 mol), add 300 mL of methanol under stirring conditions, and add sodium methoxide (102.9 g, 1.91 mol), After the addition, the temperature was raised to 60-70°C, cuprous chloride (1.58g, 0.016mol) was added, the temperature was raised to 90-95°C, after the reaction was completed, it was cooled to room temperature, the insoluble solid was filtered out, and the filtrate was added to sulfuric acid (0.76 mL, 0.95mol / L), stirring and crystallizing overnight, and then filtering out the solid, and vacuum-drying the obtained solid at 45°C for 8 hours to obtain 44.3 g of off-white solid.

[0045] The reaction formula is as follows:

[0046]

[0047] Purification of 1,3,5-trimethoxybenzene

[0048] Add 200mL of water to the crude 1,3,5-trimethoxybenzene (20g, 0.012mol) obtained in the reaction, stir for 2 hours and filter out the solid, add ...

Embodiment 2

[0067] Catalyst selects cuprous iodide (the mol ratio of catalyst and reaction substrate is the same as embodiment 1), and the remainder is the same as embodiment 1.

[0068]

[0069] Obtained off-white solid 16.2 g of off-white solid with a purity of 98.5%.

Embodiment 3

[0071] The reaction substrate is selected from 1,3,5-triiodobenzene, the catalyst is selected from cuprous iodide (the molar ratio of the catalyst to the reaction substrate is the same as in Example 1), and the remainder is the same as in Example 1.

[0072]

[0073] Obtained off-white solid 16.1 g of off-white solid with a purity of 99.0%.

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Abstract

The invention relates to a preparation method of 1, 3, 5-trimethoxybenzene, which is characterized by comprising the step of reacting a reaction substrate with sodium methoxide under the catalysis ofcuprous halide, wherein the reaction substrate is selected from one of 1, 3, 5-trichlorobenzene, 1, 3, 5-tribromobenzene, 1, 3, 5-triiodobenzene, 1, 3, 5-trimethylsulfonyl benzene and 1, 3, 5-tri (trifluoromethylsulfonyl) benzene, and the solvent of the reaction is selected from one or two of N, N-dimethyl amide, N, N-diethyl amide, methanol, ethanol, isopropanol and dimethyl sulfoxide. The methodis simple and convenient to operate and good in reproducibility, and the prepared finished product is stable in quality and high in purity.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to a preparation method of 1,3,5-trimethoxybenzene. Background technique [0002] 1,3,5-trimethoxybenzene, alias trimethylphloroglucinol, etc., CAS registration number: 621-23-8, molecular formula C9H12O3. 1,3,5-trimethoxybenzene is phloroglucinol injection One of the main components in the liquid, the latter is widely used in the treatment of smooth muscle spasm, with the characteristics of rapid antispasmodic effect, significant effect, and no toxic side effects. [0003] In the prior art, the methods for preparing 1,3,5-trimethoxybenzene include: phloroglucinol methylation method, trihaloanisole etherification method, etc., in the trihaloanisole etherification method, etc., However, these methods often have disadvantages such as cumbersome operation, difficult acquisition of raw materials, high preparation cost, low yield, and low purity. As Chinese patent (CN1491927A) just d...

Claims

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Application Information

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IPC IPC(8): C07C41/16C07C43/205
CPCC07C41/16C07C43/2055
Inventor 何凌云陈彬辉余洋汪洋
Owner NANJING CORE TECH CO LTD
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