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Method for preparing p-methoxycinnamic acid

A technology of methoxycinnamic acid and methoxyhalobenzene, which is applied in the field of preparation of intermediate p-methoxycinnamic acid, can solve the problems of difficult industrial production, high price, and difficulty in obtaining, and achieve easy control, Easy to achieve industrial production and reduce pollution

Active Publication Date: 2019-12-06
ANHUI SHENGNUOBEI CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material p-methoxyaniline used in this method is not easy to obtain, and the catalyst palladium salt and organic phosphine ligand used are more expensive, and this method has potential danger and will produce a large amount of three wastes in the process of preparing diazonium salt, so it is difficult to realize Industrial production

Method used

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  • Method for preparing p-methoxycinnamic acid
  • Method for preparing p-methoxycinnamic acid
  • Method for preparing p-methoxycinnamic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Salt-forming reaction: Add 19.1g (0.18mol) Na to a 0.5L clean batching kettle 2 CO 3 , 150g tap water, start stirring, slowly add 26g (0.36mol) acrylic acid, after the addition is complete, keep stirring until there is no bubble in the kettle (produce about 7.94gCO 2 gas), clear and transparent.

[0070] Coupling reaction: Add the prepared sodium acrylate solution into a 1L clean autoclave, add 11.87mg Cu 2 (OH) 2 CO 3 (179.33ppm rel.to BA), keep stirring for 10min. In the autoclave, add 19.1g (0.18mol) Na 2 CO 3 , 250g tap water, keep stirring for 10min. Add 56g (0.30mol) 4-methoxybromobenzene (BA) and 3.8mg (17.2×10 -6 mol) BHT, close the feed port of the autoclave, use N 2 Replace 5 times, raise the temperature to 150°C, and keep warm until the pressure no longer increases (the highest pressure is 1.5MPa), which takes about 2 hours. Stirring is accompanied during the reaction, and the stirring speed is maintained at 1200 r / min. Turn off the heating device,...

Embodiment 2

[0074] Salt-forming reaction: add 20.6g (0.19mol) Na to a 0.5L clean batching kettle 2 CO 3 , 150g tap water, start stirring, slowly add 26g (0.36mol) acrylic acid, after the addition is complete, keep stirring until there is no bubble in the kettle and it is clear and transparent.

[0075] Coupling reaction: Add the prepared sodium acrylate solution into a 1L clean autoclave, add 9.97mg Cu 2 (OH) 2 CO 3 (150.80ppm rel.to BA), keep stirring for 10min. Add 15.0g (0.18mol) NaHCO respectively in the autoclave 3 , 250g tap water, keep stirring for 10min. Add 56g (0.30mol) p-bromoanisole (BA) and 4.2mg (23.3×10 -6 mol) BHA, close the feed port of the autoclave, use N 2 Replace 5 times, raise the temperature to 160°C, and keep warm until the pressure no longer increases, about 2 hours. Stirring was accompanied during the reaction, and the stirring speed was kept at 1000 r / min. Turn off the heating device, turn on the condensed water to lower the temperature to 85°C, evacuat...

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Abstract

The invention relates to a method for preparing p-methoxycinnamic acid. The method comprises the following steps: a salt forming reaction: reacting acrylic acid with an alkaline inorganic salt to obtain acrylate; and a coupling reaction: reacting 4-methoxyhalobenzene and acrylate, and carrying out acidifying to obtain p-methoxycinnamic acid. According to the method, an organic phase reaction system is changed into a water phase reaction system; a brand-new, efficient and low-cost catalyst is adopted for catalysis; so high-quality p-methoxycinnamic acid is prepared at low cost, and the preparedp-methoxycinnamic acid has HPLC content of no less than 99.5%, single impurity content of no more than 0.2% and total impurity content of no more than 0.5%.

Description

technical field [0001] The invention belongs to the technical field of daily chemicals, and relates to a preparation method of an organic intermediate, in particular to a preparation method of the intermediate p-methoxycinnamic acid. Background technique [0002] Isooctyl p-methoxycinnamate (OMC) is one of the most commonly used sunscreen agents in the world at present. It is a good absorber of ultraviolet rays in the UVB area and can effectively prevent ultraviolet rays of 280-330nm. Stimulating, good safety, and good solubility to oily raw materials, it is almost an ideal sunscreen agent, so it is widely used in the fields of daily chemicals, plastics, rubber and paints. [0003] One of the current industrial preparation routes for OMC is the esterification of p-methoxycinnamic acid and isooctyl alcohol under acidic catalyst conditions. The synthesis of the key intermediate p-methoxycinnamic acid is the key to the industrialization of this route. The CAS number of p-metho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/64C07C51/367C07C51/43C07C57/04C07C51/41
CPCC07C51/367C07C51/412C07C51/43C07C57/04C07C59/64
Inventor 刘启发王荣杨健王中孝张亚楠
Owner ANHUI SHENGNUOBEI CHEM TECH
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