Method for preparing beta-naphthoxyacetic acid

A technology of naphthyloxyacetic acid and chloroacetic acid, which is applied in the field of preparation of β-naphthyloxyacetic acid, can solve the problems of expensive raw materials, unfavorable industrial production, and low yield, and achieve the effect of low price

Inactive Publication Date: 2012-03-28
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, there are also literature reports to prepare β-naphthyloxyacetic acid by methods such as microwave radiation method and phase transfer catalyst, but these methods either have a long reaction time, low yield or expensive raw materials, which are not conducive to industrial production.

Method used

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  • Method for preparing beta-naphthoxyacetic acid

Examples

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Comparison scheme
Effect test

Embodiment 1

[0017] In the first step, add 3g of sodium hydroxide and 7ml of water into the reactor and stir to dissolve the sodium hydroxide, then add 0.02mol β-naphthol, stir quickly to completely dissolve the β-naphthol, and react with β-naphthol to form sodium phenate.

[0018] In the second step, add 0.01mol chloroacetic acid and gradually raise the temperature to 80°C. At this time, all the solids are dissolved, and a dark brown solution is obtained. Continue to stir for 10 minutes, and a beige solid precipitates. Stop stirring and cool to room temperature, and add 30% HCl solution while stirring. Adjust the pH to 1; the color of the solid becomes darker, filter, wash with water, and recrystallize with benzene or 50% alcohol-water to obtain white crystals that are β-naphthyloxyacetic acid. Calculated by weighing, the yield is 57%.

Embodiment 2

[0020] In the first step, add 3g of sodium hydroxide and 7ml of water into the reactor and stir to dissolve the sodium hydroxide, then add 0.02mol β-naphthol, stir quickly to completely dissolve the β-naphthol, and react with β-naphthol to form sodium phenate.

[0021] In the second step, add 0.025mol chloroacetic acid and gradually raise the temperature to 80°C. At this time, all the solids are dissolved to obtain a dark brown solution. Continue to stir for 10 minutes and a beige solid will precipitate. Stop stirring and cool to room temperature. Add 30% HCl solution while stirring. Adjust the pH to 1; the color of the solid becomes darker, filter, wash with water, and recrystallize with benzene or 50% alcohol-water to obtain white crystals that are β-naphthyloxyacetic acid. Calculated by weighing, the yield is 65%.

Embodiment 3

[0023] In the first step, add 3g of sodium hydroxide and 7ml of water into the reactor and stir to dissolve the sodium hydroxide, then add 0.02mol β-naphthol, stir quickly to completely dissolve the β-naphthol, and react with β-naphthol to form sodium phenate.

[0024] In the second step, add 0.045mol chloroacetic acid and gradually heat up to 80°C. At this time, all the solids are dissolved to obtain a dark brown solution. Continue to stir for 10 minutes and a beige solid will precipitate. Stop stirring and cool to room temperature. Add 30% HCl solution while stirring. Adjust the pH to 1; the color of the solid becomes darker, filter, wash with water, and recrystallize with benzene or 50% alcohol-water to obtain white crystals that are β-naphthyloxyacetic acid. Calculated by weighing, the yield is 77%.

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Abstract

The invention relates to a method for preparing beta-naphthoxyacetic acid, comprising the following steps: step A, adding a g of sodium hydroxide in a reactor, adding b ml of water in the reactor with stirring to dissolve sodium hydroxide, then adding c mol of beta-naphthol with rapidly stirring; step B, adding d mol of chloroacetic acid and gradually heating up to 80 DEG C to obtain a dark brown solution when the solid is completely dissolved, continuously stirring for 10 min until cream-colored solid precipitates, after stopping stirring and slightly cooling, adding a 30 % HCL solution with stirring to regulate the pH value to 1; filtering and washing when the solid turns dark, and carrying out recrystallization by using benzene or 50 % alcohol-water to obtain white crystals, that is, beta-naphthoxyacetic acid. According to the invention, nonorganic base and water are used as solvent to prepare beta-naphthoxyacetic acid; the reaction temperature is 80 DEG C, thus the reaction is mild and easy to control; the reaction time is only 10 min; the raw materials used herein are cheap; when the addition of chloroacetic acid is 3 times the addition of beta-naphthol, the yield reaches 87 %.

Description

【Technical field】 [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing beta-naphthyloxyacetic acid. 【Background technique】 [0002] β-Naphthyloxyacetic acid is a widely used plant growth regulator. It is widely used in crop production. For example, it is used to promote the rooting of cuttings of fruit trees and flowers, increase the fruit setting rate and yield of melons and fruits, etc., and it is also an intermediate of drug synthesis. Therefore, it is of great practical significance for industrial and agricultural production to study and explore new technologies for synthesizing naphthaleneoxyacetic acid to improve production capacity. The classic method of synthesizing β-naphthyloxyacetic acid is obtained by condensation of corresponding sodium naphthol and sodium chloroacetate in water, but this synthetic method reaction condition is harsh, and reaction temperature is higher, and the time is longer, and productive r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/70C07C51/367
Inventor 刘玉婷苏宝君王捷尹大伟冯丽元方
Owner SHAANXI UNIV OF SCI & TECH
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