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Synthesis method of 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one

A technology of dimethoxyphenyl and dimethoxyphenylacetate, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve toxicity, is not suitable for large-scale production, and is difficult to Handling and other problems, to achieve the effect of mild reaction, suitable for large-scale production, and simple operation

Inactive Publication Date: 2020-05-08
苏州汉德创宏生化科技有限公司
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, the preparation of the compound 1-(4-hydroxyl-3,5-dimethoxyphenyl)ethan-1-one has been reported in the literature. In the patent CN102627546, 2,6-dimethoxyphenol is used as The target product was obtained by reacting the raw material with acetic acid in phosphorus pentoxide and 70% phosphoric acid aqueous solution. However, 1-(4-hydroxy-3,5-dimethoxyphenyl)ethane-1 -ketone, but this route adopts toxic and corrosive phosphorus pentoxide, which is not easy to handle, causes environmental pollution, and is not suitable for large-scale production

Method used

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  • Synthesis method of 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one
  • Synthesis method of 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one
  • Synthesis method of 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Step 1: Synthesis of 2,6-dimethoxyphenol.

[0027]

[0028] At room temperature, add hexamethylphosphoramide (HMPT, 640 g, 3.6 mol), NaH (142.9 g, 6.0 mol) into xylene (600 mL), gradually raise to 75 ° C, and drop Add N-methylaniline (382 g, 3.6 mol), and continue stirring for 20 minutes after the dropwise addition; then add 1,2,3-trimethoxybenzene (300 g, 1.8 mol) and xylene (100 mL) dropwise , after the dropwise addition was completed, the reaction was stirred at 70° C., and the reaction was monitored by TLC. After the reaction is complete, the reaction liquid is quenched with ice water, and the resulting solid is filtered, and the water phase is combined with the solid, and the pH is adjusted to 2 with HCl (6M), and the pH is adjusted with dichloromethane (chloroform, 1,2-dichloroethane can also be used). alkane, ethyl acetate, tert-butyl methyl ether, methyl tetrahydrofuran) to extract the aqueous phase; the organic phase was dried (Na 2 SO 4 ) and concentrate...

Embodiment 2

[0039] Step 1: Synthesis of 2,6-dimethoxyphenol.

[0040]At room temperature, add hexamethylphosphoramide (640 g, 3.6 mol), NaH (214.4 g, 9.0 mol) into dichloromethane (600 mL), gradually raise to 50 ° C, and dropwise add N-Methylaniline (382 g, 3.6 mol), continue to stir for 20 minutes after the dropwise addition; then add dropwise a solution of 1,2,3-trimethoxybenzene (300 g, 1.8 mol) and dichloromethane (100 mL) , after the dropwise addition was completed, the reaction was stirred at 50° C., and the reaction was monitored by TLC. After the reaction was completed, the reaction solution was quenched with ice water, and the resulting solid was filtered, the aqueous phase was combined with the solid, adjusted to pH 2 with HCl (6M), and the aqueous phase was extracted with dichloromethane; the organic phase was dried (Na 2 SO 4 ) and concentrated to obtain 236 g of 2,6-dimethoxyphenol, yield: 85%.

[0041] Step 2: Synthesis of 2,6-dimethoxyphenylacetate.

[0042] At room tem...

Embodiment 3

[0046] Step 1: Synthesis of 2,6-dimethoxyphenol.

[0047] At room temperature, add hexamethylphosphoramide (960 g, 5.4 mol), NaH (142.9 g, 6.0 mol) into tetrahydrofuran (600 mL), gradually raise the temperature to 100 ° C, and drop N- Methylaniline (573 g, 5.4 mol), continue to stir for 20 minutes after the dropwise addition; then add dropwise 1,2,3-trimethoxybenzene (300 g, 1.8 mol) and tetrahydrofuran (100 mL) solution, dropwise Afterwards, the reaction was stirred at 100° C., and the reaction was monitored by TLC. After the reaction was completed, the reaction solution was quenched with ice water, and the resulting solid was filtered, the aqueous phase was combined with the solid, adjusted to pH 2 with HCl (6M), and the aqueous phase was extracted with dichloromethane; the organic phase was dried (Na 2 SO 4 ) and concentrated to obtain 222 g of 2,6-dimethoxyphenol, yield: 80%.

[0048] Step 2: Synthesis of 2,6-dimethoxyphenylacetate.

[0049] At room temperature, add 2,...

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Abstract

The invention relates to a synthesis method of 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one. The synthesis method is characterized by comprising the following steps: removing a 2-methyl group from 1,2,3-trimethoxybenzene serving as an initial raw material to obtain 2,6-dimethoxyphenol; then carrying out a reaction on 2,6-dimethoxyphenol and an acetyl group to obtain 2,6-dimethoxyphenylacetate; andfinally, rearranging 2,6-dimethoxyphenol to obtain the 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one. Compared with the prior art, the method adopts non-toxic and environment-friendly materials as rawmaterials, is simple to operate and mild in reaction, does not cause environmental pollution or harm to operators, and is suitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and relates to a preparation process of a pharmaceutical intermediate, in particular to a synthesis method of compound 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one. Background technique [0002] 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one is an important structural unit in the field of drug synthesis, widely exists in many drug structures, and can be further reacted with aldehydes to prepare ketone compounds, etc. [0003] At present, the preparation of the compound 1-(4-hydroxyl-3,5-dimethoxyphenyl)ethan-1-one has been reported in the literature. In the patent CN102627546, 2,6-dimethoxyphenol is used as The target product was obtained by reacting the raw material with acetic acid in phosphorus pentoxide and 70% phosphoric acid aqueous solution. However, 1-(4-hydroxy-3,5-dimethoxyphenyl)ethane-1 -ketone, but this route adopts phosphorus pentoxide which is toxic and corrosive, which is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/54C07C49/84
CPCC07C45/54C07C67/10C07C41/26
Inventor 茅仲平马东旭张磊
Owner 苏州汉德创宏生化科技有限公司
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