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Preparation method of hydroxybenzyl cyanide

A technology of hydroxyphenylacetonitrile and hydroxyphenylacetamide, which is applied in the field of preparation of p-hydroxyphenylacetonitrile, can solve the problems of high waste treatment cost, serious equipment corrosion, complicated treatment, etc., and achieve the advantages of simple operation, short route and mild reaction conditions Effect

Inactive Publication Date: 2012-09-19
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are many steps in the reaction process and the treatment is complicated. A large amount of concentrated sulfuric acid and concentrated nitric acid are used in the reaction process, which not only seriously corrodes the equipment, but also produces a large amount of three wastes, which is expensive to treat.

Method used

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  • Preparation method of hydroxybenzyl cyanide
  • Preparation method of hydroxybenzyl cyanide
  • Preparation method of hydroxybenzyl cyanide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 5 grams (0.033mol) of p-hydroxyphenylacetamide, 0.41 grams (1.65mmol) of dibutyltin oxide, 0.10 grams of ionic liquid N-picoline bromide and 50 mL of dry toluene in a 100 mL single-necked bottle, and the reaction mixture The reaction was stirred at reflux. 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 19 hours of reaction, the reaction was completed, and the dibutyltin oxide and ionic liquid were removed by filtration while it was hot (which can be recycled and reused). After suction filtration and drying, 4.10 g of p-hydroxybenzonitrile was obtained with a yield of 94.2% and a purity of 98.7% by gas phase analysis.

[0024] m.p.: 69-71°C;

[0025] 1 HNMR (CDCl 3 , 400M), TMS): δ3.63 (s, 2H), 6.51 (s, br, 1H), 6.85-6.87 (d, 2H), 7.15-7.17 (d, 2H).

[0026] 13 CNMR (100M, CDCl 3 ,) δ 155.8, 129.3, 121.3, 118.6, 116.2, 22.8. ...

Embodiment 2

[0028] Add 10 grams (0.066mol) of p-hydroxyphenylacetamide, 0.82 grams (3.3mmol) of dibutyltin oxide, 0.20 grams of ionic liquid N-butylpyridine bromide and 120 mL of dry toluene in a 250 mL single-necked bottle, and the reaction mixture The reaction was stirred at reflux. The progress of the reaction was detected by TLC. After 19 hours of reaction, the reaction was completed, and the dibutyltin oxide and ionic liquid were removed by filtration while it was hot (which can be recycled and reused). After suction filtration and drying, 8.60 g of p-hydroxybenzonitrile was obtained with a yield of 97.7% and a purity of 98.8% by gas phase analysis.

Embodiment 3

[0030] Add 10 grams (0.066mol) of p-hydroxyphenylacetamide, 0.82 grams (3.3 mmol) of dibutyltin oxide, 0.20 grams of 1-methyl-3-ethylimidazolium bromide and 120 mL of dry toluene into a 250 mL single-necked bottle , the reaction mixture was stirred under reflux. The progress of the reaction was detected by TLC. After 18 hours of reaction, the reaction was completed, and the dibutyltin oxide and the ionic liquid were removed by filtration while hot (which can be recycled and reused). After suction filtration and drying, 8.50 g of p-hydroxybenzonitrile was obtained with a yield of 96.6% and a purity of 98.8% by gas phase analysis.

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Abstract

The invention belongs to the field of organic chemical synthesis and particularly relates to a preparation method of hydroxybenzyl cyanide. The preparation method of the hydroxybenzyl cyanide comprises the following steps: taking P-hydroxyphenylacetamide as a raw material and carrying out dehydration reaction on the P-hydroxyphenylacetamide in an organic solvent under the condition that dibutyltin oxide and an ion liquid compound exist to obtain the hydroxybenzyl cyanide, wherein the organic solvent selects from toluene, ethylbenzene, isopropylbenzene, n-butyl benzene, benzene, nitrobenzene, chlorobenzene and mixture thereof. In the preparation method, the hydroxybenzyl cyanide is prepared through taking the P-hydroxyphenylacetamide as the raw material, the dibutyltin oxide as a dewatering agent, the ion liquid compound as a catalyst, and the toluene and the like as a solvent and a dehydrating agent. The preparation method has the characteristics of mild reaction condition, no pollution and high yield; the dibutyltin oxide and the ion liquid can be recycled for above 10 times, and the yield is basically kept unchanged.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and more specifically, relates to a preparation method of 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 three synthetic routes are mainly used to synthesize: [0004] (1) Taking phenylacetonitrile as raw material synthesis: this process uses phenylacetonitrile as raw material, and obtains p-hydroxyphenylacetonitrile ("Synthesis of Actarit", "Hebei Province" through four steps of nitration, reduction, diazotization and hydrolysis) University Journal: Natural Science Edition, No. 2, 2008, 178-200.), the total ...

Claims

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Application Information

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IPC IPC(8): C07C255/36C07C253/20
CPCY02P20/54
Inventor 宗乾收祝兴龙吴建一包琳
Owner JIAXING UNIV
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