Synthetic method of p-(2-methoxyethyl) phenol

A technology of methoxyethylphenol and synthesis method, which is applied in chemical instruments and methods, preparation of ether from alkylene oxide, preparation of organic compounds, etc., can solve the problem of large amount of "three wastes" and low yield of methoxyethylphenol and other problems, to achieve the effect of high product purity, reduced post-processing difficulty and good product stability

Inactive Publication Date: 2018-10-23
LIHAI CHEM IND CO LTD OF JIANGSU JINQIAO SALT & CHEM GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of p-methoxyethylphenol by this method has the disadvantages of low yield and large amount of "three wastes".

Method used

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  • Synthetic method of p-(2-methoxyethyl) phenol
  • Synthetic method of p-(2-methoxyethyl) phenol
  • Synthetic method of p-(2-methoxyethyl) phenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 200g of p-chlorophenol, 429.6g of potassium carbonate, and 378g of DMF to a 1000mL three-necked flask, stir and raise the temperature to 80°C, stir for 1h, add 208g of benzyl chloride dropwise (dropping time is about 0.5h); react at 105°C for 1h, cool to 80°C, Filter, distill off DMF under reduced pressure, and cool to room temperature to obtain 327.5 g of p-benzyloxychlorobenzene with a yield of 96.31%. Purity 98.4% (HPLC).

Embodiment 2

[0028] Other conditions are with embodiment 1, check the experiment of different benzyl chloride, salt of wormwood consumption, experimental result is shown in Table 1.

[0029] Table 1 reaction varies with the amount of benzyl chloride

[0030]

Embodiment 3

[0032] Add 14.82g of magnesium powder and 189g of methyl tetrahydrofuran into a three-necked flask, heat to reflux, add dropwise a solution of methyl tetrahydrofuran in which 122g of p-benzyloxychlorobenzene is dissolved, add 1-2 grains of iodine to trigger, and reflux for 2 hours after the dropwise addition. The temperature was lowered to 0°C, and 49.41 g of ethylene oxide was added dropwise. After the reaction, pour it into water, separate methyl tetrahydrofuran, concentrate and crystallize to obtain 98.5 g of p-benzyloxyphenethyl alcohol, with a purity of ≥95% (HPLC).

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Abstract

The invention discloses a synthetic method of p-(2-methoxyethyl) phenol. The target product p-(2-methoxyethyl) phenol is prepared from p-chlorophenol serving as a starting material through phenolic hydroxyl group protection, a Grignard reaction, methylation and a hydrogenation debenzylation reaction. The starting material can be applied to a next-step reaction through simple filtering operation after a methylation reaction without the need of other operations. According to the synthetic method, the p-chlorophenol is taken as the starting for synthesizing the p-(2-methoxyethyl) phenol, so thatthe treatment difficulty is lowered, the reaction time is shortened, and the product has high purity, high yield and high stability.

Description

technical field [0001] The invention relates to a method for preparing p-methoxyethylphenol, which belongs to the field of synthesis of pharmaceutical intermediates. Background technique [0002] p-methoxyethylphenol is the key intermediate of the synthetic drug metoprolol, and its structural formula is as follows: [0003] [0004] P-methoxyethylphenol is generally obtained by using phenylethyl alcohol as a starting material, and is obtained through multi-step reactions and purifications such as methyl etherification, nitration, reduction, diazotization and hydrolysis. Synthesis of p-methoxyethyl phenol by this method has disadvantages such as low yield and large amount of "three wastes". Contents of the invention [0005] The object of the present invention is to provide a kind of synthetic method of p-methoxyethylphenol, and this method reaction condition is gentle, and productive rate is high, and environmental protection, aftertreatment step is few. [0006] The ...

Claims

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Application Information

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IPC IPC(8): C07C41/16C07C43/225C07C41/02C07C43/23C07C43/205C07C41/26C07C43/178
CPCC07C41/02C07C41/16C07C41/26C07C43/225C07C43/23C07C43/2055C07C43/1783
Inventor吉凤成姜红来韩勇申卫卫臧涵蒋校
OwnerLIHAI CHEM IND CO LTD OF JIANGSU JINQIAO SALT & CHEM GRP