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Preparation method of aromatic methyl ether compound

A technology for aromatic compounds and aromatic methyl ethers, applied in ether preparation, organic chemistry, etc., can solve problems such as adverse impacts on production costs, unfavorable product quality, impacts, etc., to reduce the possibility of debromination reduction reactions and reduce production Cost, effect of improving product quality and yield

Inactive Publication Date: 2009-11-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0006] (2) For the polymethoxylation reaction containing 2 to 3 bromine atoms, not only the reduction reaction of debromination can occur, but also the polymethoxylation reaction cannot be carried out completely and thoroughly, which has an adverse effect on product quality;
[0007] (3) Due to the decomposition of DMF in the reaction process, the recovered methanol needs to go through a series of refining processes before it can be used mechanically, which has a negative impact on production costs

Method used

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  • Preparation method of aromatic methyl ether compound
  • Preparation method of aromatic methyl ether compound
  • Preparation method of aromatic methyl ether compound

Examples

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Embodiment 1

[0026] Embodiment 1 synthesizes syringaldehyde

[0027] See attached figure 2 137.8g, 29% sodium methoxide methanol solution (0.74mol), 56.0g of 4-hydroxyl-3,5-dibromobenzaldehyde (0.20mol), 2.8g of chlorinated methoxide were added successively in a 500mL autoclave Copper (0.028 mol). Seal the autoclave, feed about 2.8 g of carbon monoxide (0.10 mol), stir, heat up to 120° C. and keep it warm for 3 hours, stop heating and cool to room temperature. Carefully open the autoclave, transfer the reaction mixture to a flask, distill and recover methanol, add 250 mL of water, and raise the temperature to 90°C to dissolve the sodium phenolate salt of 4-hydroxy-3,5-dimethoxybenzaldehyde. The catalyst was removed by hot filtration, the filtrate was cooled to room temperature, acidified with dilute hydrochloric acid to pH=5.0-6.0, and a large amount of white solid was precipitated. Filter and dry the filter cake to obtain 35.2 g of white syringaldehyde (4-hydroxy-3,5-dimethoxybenzalde...

Embodiment 2

[0030] Synthesis of 3,4,5-trimethoxybenzaldehyde in embodiment 2

[0031] See attached image 3 137.8g, 29% sodium methoxide methanol solution (0.74mol), 56.0g of 4-hydroxyl-3,5-dibromobenzaldehyde (0.20mol), 2.8g of chlorinated methoxide were added successively in a 500mL autoclave Copper (0.028 mol), 5.0 g of methyl formate (0.083 mol). Seal the autoclave, stir, heat up to 120°C and keep it warm for 3 hours, stop heating and cool to room temperature. Carefully open the autoclave, transfer the reaction mixture to a flask, distill and recover methanol, add 100mL of water, raise the temperature to 90°C to dissolve the eugenalphenol sodium salt, and freeze to 10°C to crystallize the phenol sodium salt. Filter to separate the filter cake of eugenol sodium salt. Add 250 mL of water to the filter cake of syringaldehyde phenol sodium salt, and heat up to 90° C. to dissolve the phenol sodium salt. Heat filtration removes catalyzer, the sodium phenate mother liquor of filtering is...

Embodiment 3

[0034] Example 3 Synthesis of 3,4,5-trimethoxytoluene

[0035] See attached Figure 4100.5 g, 29% sodium methoxide methanol solution (0.54 mol), 56.0 g of 4-methoxy-3,5-dibromotoluene (0.20 mol), 2.8 g of chlorinated Cuprous (0.028 mol), 5.0 g of methyl formate (0.083 mol). Seal the autoclave, stir, heat up to 120°C and keep it warm for 3 hours, stop heating and cool to room temperature. Carefully open the autoclave, transfer the reaction mixture to a flask, distill off the recovered methanol and distill the residue under reduced pressure, collect the fraction with a boiling point (bp) of 102-104°C / 450Pa, and the product solidifies to give colorless 3, 4, 5 - 34.7 g of trimethoxytoluene solid, melting point (mp) 33-35° C., yield 95.3%. HPLC test purity ≥ 99.0%.

[0036] 1 H NMR (500MHz, CDCl 3 ): 2.32 (s, 3H, CH 3 ), 3.82 (s, 3H, OCH 3 ), 3.85(s, 6H, OCH 3 ), 6.40 (s, 2H, ArH).

[0037] EI-MS m / z: 182 (M + , 85), 167(100), 139(37), 124(20), 109(17).

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Abstract

The invention discloses a preparation method of an aromatic methyl ether compound, which comprises the following steps: inactive aromatic bromides are dissolved in an excessive sodium methoxide methanol solution in a pressure kettle and cuprous salt as a primary catalyst and carbon monoxide as an auxiliary catalyst or cuprous salt as a primary catalyst and methyl formate as an auxiliary catalyst are added in the pressure kettle, the sealed pressure kettle completes methoxylation displacement reaction under the condition of being heated; high-purity methanol is recycled and outcome is simply separated to obtain the aromatic methyl ether compound which has high yield and purity. The invention has the advantages that the efficiency of methoxylation is enhanced, thereby improving the quality and the yield of the product and also reducing the production cost.

Description

【Technical field】 [0001] The invention relates to the technical field of fine organic synthesis, in particular to a method for preparing an aromatic methyl ether compound through the methoxylation reaction of an inactive brominated aromatic compound. 【Background technique】 [0002] If the aromatic ring of brominated aromatic compounds does not contain a strong electron-withdrawing group such as nitro (-NO 2 ), nitrile (-CN), trifluoromethyl (-CF 3 ), fluorine atoms (-F), etc., such compounds are usually called non-reactive brominated aromatic compounds. Under the action of a catalyst, inactive brominated aromatic compounds undergo a methoxylation reaction with sodium methoxide to generate the corresponding aromatic methyl ether compounds. This is a common type of unit reaction in fine organic synthesis. It is used in medicine, pesticides, It is widely used in the synthesis of fine chemicals such as dyes and fragrances. [0003] The methoxylation reaction of inactive bromi...

Claims

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Application Information

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IPC IPC(8): C07C41/01C07C43/205
Inventor 冀亚飞金文虎万欢段梅莉许煦
Owner EAST CHINA UNIV OF SCI & TECH
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