Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing para hydroxybenzene acetonitrile

A technology of hydroxyphenylacetonitrile and p-hydroxyphenylethanol, which is applied in the field of organic chemical synthesis, can solve the problem of high price, and achieve the effects of short route, mild reaction conditions and high yield

Inactive Publication Date: 2013-12-18
JIAXING UNIV
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process has the characteristics of mild reaction conditions, no pollution, catalyst recycling and high yield. However, the price of p-hydroxyphenylacetamide raw materials is relatively high at present, which leads to the price of the product p-hydroxyphenylacetonitrile.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing para hydroxybenzene acetonitrile
  • Method for preparing para hydroxybenzene acetonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 4.56 g (0.033 mol) of p-hydroxyphenethyl alcohol and 8.8 mL (0.132 mol) of ammonia water (28 wt%) into a 100 mL three-necked flask (equipped with a thermometer, magnetic stirring, reflux condenser and constant pressure dropping funnel), and the reaction mixture Heat to 50°C to dissolve p-hydroxyphenethyl alcohol, then slowly add 36.3mL (0.073mol) of 6.5wt% sodium hypochlorite aqueous solution dropwise, and control the reaction temperature at 50°C. Reaction adopts TLC detection reaction to carry out degree, developing agent sherwood oil / ethyl acetate (volume ratio 2:1), the R of p-hydroxyphenylacetonitrile f About = 0.6. After 20 hours of reaction, the reaction was completed, and the reaction solution was cooled to about 0°C to crystallize. After suction filtration and drying, 4.13 g of p-hydroxybenzonitrile was obtained, with a yield of 95.0% and a purity of 98.8% by gas chromatography.

[0025] m.p.: 69-71°C;

[0026] 1 HNMR (CDCl 3 , 400M), TMS): δ3.63 (s, 2H...

Embodiment 2

[0028] Add 9.12 grams (0.066mol) of p-hydroxyphenylethyl alcohol and 17.6mL (0.264mol) of ammonia water (28wt%) into a 250mL three-neck flask (equipped with a thermometer, magnetic stirring, reflux condenser and constant pressure dropping funnel), and the reaction mixture Heat to 60°C to dissolve p-hydroxyphenethyl alcohol. Then, 99.0 mL (0.198 mol) of 6.5 wt % sodium hypochlorite aqueous solution was slowly added dropwise, and the reaction temperature was controlled at 60 °C. The progress of the reaction was detected by TLC. After 10 hours of reaction, the reaction was completed, and the reaction solution was cooled to about 0°C to crystallize. After suction filtration and drying, 8.63 g of p-hydroxybenzonitrile was obtained with a yield of 98.2% and a purity of 99.0% by gas chromatography.

Embodiment 3

[0030] Add 9.12 grams (0.066mol) of p-hydroxyphenylethyl alcohol and 16.0mL (0.30mol) of ammonia water (35wt%) into a 250mL three-necked flask (equipped with a thermometer, magnetic stirring, reflux condenser and constant pressure dropping funnel), and the reaction mixture Heat to 60°C to dissolve p-hydroxyphenethyl alcohol. Then, 99.0 mL (0.198 mol) of 6.5 wt % sodium hypochlorite aqueous solution was slowly added dropwise, and the reaction temperature was controlled at 60 °C. The progress of the reaction was detected by TLC. After reacting for 9 hours, the reaction was completed, and the reaction solution was cooled to about 0°C to crystallize. After suction filtration and drying, 8.65 g of p-hydroxybenzonitrile was obtained with a yield of 98.4% and a purity of 99.2% by gas chromatography.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the field of organic chemical synthesis, and relates to a method for preparing para hydroxybenzene acetonitrile. The method comprises the following step: carrying out oxidation, ammoniation and reoxidation reactions on para hydroxybenzene ethanol in the presence of ammonia water and hypochlorite by taking the para hydroxybenzene ethanol as a raw material and water as a reaction medium to obtain the para hydroxybenzene acetonitrile. The process route for oxidation, ammoniation and reoxidation on the para hydroxybenzene ethanol by taking the lower-price (relative to para hydroxybenzene acetamide) para hydroxybenzene ethanol as the raw material has the characteristics of mildness in reaction condition and high yield; meanwhile, the production cost of the para hydroxybenzene acetonitrile is greatly reduced; the technical route has the characteristics of short route, easiness and convenience for operation, mildness in reaction condition and easiness for industrialized production and is a very economic, simple and convenient method for preparing the para hydroxybenzene acetonitrile.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and more specifically relates to a method for preparing p-hydroxyphenylacetonitrile. Background technique [0002] p-Hydroxyphenylacetonitrile is an important pharmaceutical intermediate and an important raw material for the synthesis of β receptor blocker atenolol (also known as atenolol). It has a large demand in domestic and foreign markets and has a good market prospect. [0003] There are few synthetic routes of p-hydroxyphenylacetonitrile reported at present, and the following four synthetic routes are mainly used to synthesize: [0004] (1) Synthesis using phenylacetonitrile as raw material: This process uses phenylacetonitrile as raw material to prepare p-hydroxybenzonitrile through four steps of nitration, reduction, diazotization and hydrolysis ("Synthesis of Actarit", "Hebei University Journal: Natural Science Edition, No. 2, 2008, 178-200.), the total yield of the four-step ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C255/36C07C253/00
Inventor 宗乾收繆程平张洋吴建一包琳
Owner JIAXING UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com