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
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This process has the characteristics of mild reaction conditions, no pollution, catalyst recycling and high yield. However, the price ...

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  • 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.

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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

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Application Information

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IPC IPC(8): C07C255/36C07C253/00
Inventor 宗乾收繆程平张洋吴建一包琳
Owner JIAXING UNIV
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