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Preparation method of o(p)-hydroxybenzonitrile

A technology of hydroxybenzonitrile and halogenated benzonitrile is applied in the field of preparation of important fine chemical intermediate o-hydroxybenzonitrile, which can solve the problems of being unsuitable for large-scale production, difficult to obtain, etc. The effect of less product and simple process

Active Publication Date: 2014-07-09
JIANGSU LIANHE CHEM TECH +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0029] The shortcoming of this method is that no matter the raw material is ortho (p) cyanoanisole or o (p) methyl anisole, it is not easy to obtain on the market, and it is not suitable for large-scale production

Method used

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  • Preparation method of o(p)-hydroxybenzonitrile
  • Preparation method of o(p)-hydroxybenzonitrile
  • Preparation method of o(p)-hydroxybenzonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054]Add 250g of sodium methoxide methanol solution with a solution concentration of 20.7% and 60g of o-chlorobenzonitrile into a 1000ml autoclave, replace the air in the autoclave with nitrogen, raise the temperature to 160°C, and the autoclave pressure to 2.5Mpa, and react in this state After 6 to 9 hours, the reaction is completed, the temperature is lowered to below 50°C, and methanol is recovered under reduced pressure (applicable), adding cold water to dissolve the residual product, filtering the insoluble matter, acidifying with 36% hydrochloric acid, and the white product o-hydroxybenzene is precipitated Amethonitrile, the content after drying is >99.0%, the mass is 50.5g, and the yield is 96.4%.

Embodiment 2

[0056] Add 258g of 28.5% sodium methoxide methanol solution and 75g of p-chlorobenzonitrile into a 1000ml autoclave. After replacing the air in the autoclave with nitrogen, the temperature is raised to 200°C, and the autoclave pressure is raised to 2.8Mpa. React in this state for 5 ~7 hours, finish the reaction, lower the temperature to below 50°C, recover methanol under reduced pressure (applicable), add cold water to dissolve the residual product, filter the insoluble matter, acidify with 36% hydrochloric acid, and precipitate the white product p-hydroxybenzonitrile, After drying, the content is >99.0%, and the mass is 62.8g. Yield 95.9%.

Embodiment 3

[0058] Add 244g of ethanol solution with a solution concentration of 25.7% sodium ethoxide and 70g of o-bromobenzonitrile in a 1000ml autoclave, replace the air in the autoclave with nitrogen, raise the temperature to 200°C, and the autoclave pressure to 3.0Mpa, and react in this state After 5-7 hours, finish the reaction, lower the temperature to below 50°C, recover ethanol under reduced pressure (applicable), add cold water to dissolve the residual product, filter the insoluble matter, acidify with 36% hydrochloric acid, and precipitate the white product o-hydroxybenzonitrile , the content after drying is >99.0%, and the mass is 43.5g. Yield 96.1%.

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Abstract

The invention provides a preparation method of o(p)-hydroxybenzonitrile which is an important fine chemical intermediate applied in medical and pesticide fields. The method comprises the steps of: reacting the raw material of o(p)-halogenated benzonitrile with an anhydrous alcohol solution of alkali metal alkoxide at a concentration of 5-50% for 1-24h in a mol ratio of 1:2-5, at a temperature of 100-250DEG C and under a pressure of 0.5-6MPa, then conducting temperature falling, cooling, reduced pressure distillation and exsolution, and adding hydrochloric acid for acidification, thus obtaining an o(p)-hydroxybenzonitrile solid. The method provided in the invention has cheap raw material, short reaction step, safe operation, high yield and less by-product, thus being suitable for business production.

Description

technical field [0001] The invention relates to a chemical synthesis method, in particular to a preparation method of o-(p)hydroxybenzonitrile, an important fine chemical intermediate widely used in the fields of medicine and pesticides. Background technique [0002] O (p) hydroxybenzonitrile is an important fine chemical intermediate. O-hydroxybenzonitrile (also known as salicylonitrile) can be used to produce Bunirolol hydrochloride, which belongs to β-receptor blocker. It is mainly used for the treatment of atrial fibrillation; supraventricular tachycardia and other arrhythmias; angina pectoris and hypertension. p-Hydroxybenzonitrile can be used in the production of benzocyano-based pesticides such as “fenonitrile”, “benzonilphos”, “bromoxynil”, “hydroxydoxynil” and “bactenil”, while p-hydroxybenzonitrile It can also be used in the fields of liquid crystal materials and fragrances. [0003] The preparation methods of ortho (p) hydroxybenzonitrile developed internationa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/53C07C253/30
Inventor 樊小彬王萍李利奎黄超习培华范晶
Owner JIANGSU LIANHE CHEM TECH
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