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Synthesis method of 4-(4-phenylbutoxy) benzoic acid

A technology of phenylbutoxy and synthesis methods, which is applied in chemical instruments and methods, preparation of carboxylic acid esters, preparation of organic compounds, etc., can solve the problems of rising market demand, low yield, unsuitable for industrial production, etc., Achieve the effect of improving yield and purity, high specific surface area, and long-term stable alcoholysis activity

Inactive Publication Date: 2018-10-23
杨程飞扬
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The market demand for 4-(4-phenylbutoxy)benzoic acid is gradually increasing, and there is no relevant report on mass production in China
The traditional preparation takes tetrahydrofuran as a raw material, and prepares 4-(4-phenylbutoxy)benzoic acid through ring opening, Fredel-Crafts alkylation, halogenation, condensation, and hydrolysis. The raw material is easy to get and the reaction is simple, but the yield is very low. It is not suitable for industrial production. Therefore, it is of great significance to develop new processes for industrial synthesis and improve the yield and purity of products.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] A kind of synthetic method of 4-(4-phenylbutoxy group) benzoic acid is characterized in that the method may further comprise the steps:

[0020] Step 1. Add 1g of catalyst P-W to a 250ml three-necked flask in sequence 2 C@NC, 1-bromo-4-phenylbutane 8.0g, DMF50ml, under mechanical stirring, add 1.8g of methylparaben, K 2 CO 3 3.6g, heated to 115°C, reacted for 11h;

[0021] Step 2, after the reaction is completed, cool to room temperature, remove K by suction filtration 2 CO 3 Solid, add 50ml water to the filtrate to make it cloudy, after stirring for 10min, add about 3mol / L HCl solution to adjust pH=2;

[0022] Step 3, extract the above system with dichloromethane, wash with ion water, and remove the solvent dichloromethane by rotary evaporation to obtain an orange liquid;

[0023] Step 4. Put the above orange liquid in a single-necked bottle, add 3.0g NaOH, 50ml water and 40ml ethanol, reflux the oil bath for 3 hours, distill off the ethanol, and adjust the pH of ...

Embodiment 2

[0033] Step 1. Add 1g of catalyst P-W to a 250ml three-necked flask in sequence 2 C@NC, 6.0g of 1-bromo-4-phenylbutane, DMF50ml, under mechanical stirring, add 1.8g of methylparaben, K 2 CO 3 3.6g, heated to 115°C, and reacted for 11h; the remaining steps were the same as in Example 1.

Embodiment 3

[0035] Step 1. Add 1g of catalyst P-W to a 250ml three-necked flask in sequence 2 C@NC, 4.0g of 1-bromo-4-phenylbutane, DMF50ml, under mechanical stirring, add 1.8g of methylparaben, K 2 CO 3 3.6g, heated to 115°C, and reacted for 11h; the remaining steps were the same as in Example 1.

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PUM

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Abstract

The invention discloses a synthesis method of 4-(4-phenylbutoxy) benzoic acid. The synthesis method uses 1-bromo-4-phenylbutane, methylparaben, K2CO3, NaOH, H3PW12O40.6H20, dicyandiamide, P-W2C@NC andtoluene as main raw materials. According to the synthesis process, the methylparaben and the 1-bromo-4-phenylbutane are enabled to be subjected to an alcoholysis reaction in presence of the catalystP-W2C@NC, so that the intermediate 4-(4-phenylbutoxy) benzoic acid is obtained. The method not only greatly increases raw material utilization rate and yield, but also enables the catalyst to be recycled, thus improving the economy of the product and being suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 4-(4-phenylbutoxy)benzoic acid, which belongs to the field of chemical synthesis. Background technique [0002] 4-(4-phenylbutoxy)benzoic acid 4-(4-phenylbutoxy)benzoic acid, CAS: 30131-16-9 is an important chemical intermediate for the synthesis of pranlukast, which is combined with 8-amino-4-oxo Substitute-2-(5-1H-tetrazolyl)-4H-1-benzopyran in dichloromethane system, pyridine as acid-binding agent, through acylation reaction to get prankast. The market demand for 4-(4-phenylbutoxy)benzoic acid is gradually increasing, and there is no relevant report on mass production in China. The traditional preparation takes tetrahydrofuran as a raw material, and prepares 4-(4-phenylbutoxy)benzoic acid through ring opening, Fredel-Crafts alkylation, halogenation, condensation, and hydrolysis. The raw material is easy to get and the reaction is simple, but the yield is very low. It is not suitable for industrial...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/31C07C69/92C07C51/09C07C65/24B01J27/22B01J27/24B01J37/08B01J37/34
CPCB01J27/22B01J27/24B01J37/086B01J37/088B01J37/343C07C51/09C07C67/31C07C69/92C07C65/24Y02P20/584
Inventor 杨程飞扬陈华奇
Owner 杨程飞扬
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