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Preparation method of 4-hydroxyphenylacetonitrile

A technology of hydroxyphenylacetonitrile and hydroxyphenylacetamide, which is applied in the field of preparation of p-hydroxyphenylacetonitrile, can solve the problems of complex treatment, many steps, and high cost of three-waste treatment, and achieves high yield, simple and easy-to-control operation, and low cost. Effect

Inactive Publication Date: 2013-06-19
QINGDAO UNIV OF SCI & TECH
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  • Abstract
  • Description
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Problems solved by technology

[0004] Prepare p-hydroxyphenylacetonitrile by diazotization method, first nitrate with benzyl nitrile to obtain p-nitrophenylacetonitrile, further reduce p-nitrophenylacetonitrile to obtain p-aminophenylacetonitrile, and obtain p-aminophenylacetonitrile through diazotization, hydrolysis and recrystallization The product, the whole reaction process has many steps, the treatment is complicated, and a large amount of sulfuric acid and nitric acid are used in the reaction process, and the cost of the three wastes generated is high, and the total yield of the reaction is only about 30%. With the increase of the price of benzyl nitrile, The product no longer has a price advantage

Method used

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  • Preparation method of 4-hydroxyphenylacetonitrile

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Effect test

Embodiment 1

[0026] Preparation of crude p-hydroxybenzonitrile

[0027] In a dry reaction flask, put 5 g of p-hydroxyphenylacetamide, 20 ml of dichloromethane, and 0.5 ml of DMF, and stir. Then add 5.5ml of thionyl chloride, and react at 35-38°C for 4 hours. After the reaction is complete, slowly add 30ml of tap water, stir for 30 minutes, evaporate dichloromethane under reduced pressure, neutralize with sodium bicarbonate to pH=3~4, crystallize in an ice bath for 1 hour, filter, wash with ice water, and dry to obtain p-hydroxybenzene Crude acetonitrile.

Embodiment 2

[0029] Preparation of p-hydroxybenzonitrile

[0030] Add 60ml of tap water into the reaction bottle, put in the crude product and an appropriate amount of activated carbon, gradually heat to 85-90°C and stir for 30 minutes to decolorize. After filtration, the filtrate was extracted three times with 30 ml of ethyl acetate. Separate the organic layer, evaporate ethyl acetate under reduced pressure, add 20 ml of distilled water to grow crystals in an ice bath, filter and dry to obtain 4.2 g of p-hydroxybenzonitrile, and the yield is 95.5%. The content is above 96.5% (HPLC), MP67-69℃. The structure was confirmed by IR and NMR spectra.

[0031] The method is simple and easy to control, high in yield and low in cost, and provides a new synthetic route for the production of p-hydroxyphenylacetonitrile.

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Abstract

The invention relates to a preparation method of 4-hydroxyphenylacetonitrile. The preparation method comprises the following steps of: putting 4-hydroxyphenylacetonitrile, methylene dichloride and DMF (Dimethyl Formamide) into a dry reaction bottle and stirring; adding thionyl chloride and reacting at the temperature of 35-38 DEG C for 4 hours; slowly adding tap water after the reaction, stirringfor 30 minutes, evaporating methylene dichloride under reduced pressure, neutralizing with sodium bicarbonate until the pH is 3-4, crystallizing in an ice bath for 1 hour, filtering, washing with icewater and drying to obtain crude 4-hydroxyphenylacetonitrile; adding tap water, the crude 4-hydroxyphenylacetonitrile and an appropriate amount of active carbon into the reaction bottle, gradually heating to 85-90 DEG C, stirring and decoloring for 30 minutes; filtering and extracting filtrate with ethyl acetate for three times; and separating an organic layer out, evaporating ethyl acetate underreduced pressure, adding distilled water for bathing and grain growing, filtering and drying to obtain 4-hydroxyphenylacetonitrile with the yield of 95.5 percent and the content of over 96.5 percent [HPLC (High Performance Liquid Chromatography)] at the temperature of MP 67-69 DEG C. The structure of the 4-hydroxyphenylacetonitrile is determined by using an infrared spectrum and a nuclear magnetic resonance map. The method has the advantages of simple and easily-controlled operation, high yield and low cost, and is a novel synthesis measure provided for the production of 4-hydroxyphenylacetonitrile.

Description

technical field [0001] The invention relates to a preparation method of medicinal chemicals, in particular to a preparation method of p-hydroxybenzonitrile. 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 prospect. [0003] The product is generally synthesized by chemical methods, and very few are extracted from traditional Chinese medicines. The chemical synthesis method mainly uses p-aminophenylacetonitrile as raw material, and is prepared by diazotization method. [0004] Prepare p-hydroxyphenylacetonitrile by diazotization method, first nitrate with benzyl nitrile to obtain p-nitrophenylacetonitrile, further reduce p-nitrophenylacetonitrile to obtain p-aminophenylacetonitrile, and obtain p-aminophenylacetonitrile through diazotization, hydrolysis...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/36C07C253/20
Inventor 吴汝林王繁业
Owner QINGDAO UNIV OF SCI & TECH