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Synthetic method of benzoic acid-2-cyano-2-phenyl methyl ester
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A technology of phenylmethyl ester and synthesis method, applied in the synthesis field of benzoic acid-2-cyano-2-phenylmethyl ester, can solve problems such as limitation of large-scale production, low total yield, long reaction steps and the like , to achieve the effect of feasibility, low preparation cost and shortened operation steps
Inactive Publication Date: 2019-04-02
荆门医药工业技术研究院 +1
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The biggest highlight of this route design is that the starting materials are cheap, which greatly reduces the synthesis cost, but the reaction steps are longer and the total yield is not high; the second type of synthesis route is to use benzoyl chloride and , but the overall yield of the reaction is not high, which limits the large-scale production
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Embodiment 1
[0015] In a 250ml small flask, add 2.9g (10mmol) of 2-bromo-2-phenylmethyl benzoate, 4.24g (10mmol) of potassiumferrocyanide, 10% tetrabutylamine bromide, 100ml of N-methylimidazole, 10% cuprous iodide, warmed up to 140 degrees, reacted for 16 hours, detected by TLC, after the reaction of the raw materials, cooled to 80 degrees, added 100 ml of ethyl acetate, refluxed for 1 hour, and stopped heating , filtered, washed 3 times with 100 ml of water, and dried to obtain 2.2 g of white solid with a yield of 92.8%.
[0018] Add 29 g (100 mmol) of benzoic acid-2-bromo-2-phenylmethyl ester, 42.4 g (100 mmol) of potassiumferrocyanide, 10% tetrabutylamine bromide, 200 ml to a 500 ml small flask of N-butylimidazole, 10% cuprous iodide, warmed up to 100 degrees, reacted for 24 hours, detected by TLC, cooled to 80 degrees, added 150 ml of ethyl acetate, refluxed for 1 hour, stopped heating, filtered, respectively used Washed three times with 200 ml of water and dried to obtain 18 g of white solid with a yield of 76%.
Embodiment 3
[0020] In a 500ml flask, add 29g (100mmol) of 2-bromo-2-phenylmethyl benzoate, 35.6g (400mmol) of cuprous cyanide, 10% tetrabutylamine bromide, 200ml of N -Ethyl imidazole, 10% cuprous iodide, warmed up to 140 degrees, reacted for 16 hours, detected by TLC, after the reaction of the raw materials, cooled to 80 degrees, added 150 ml of ethyl acetate, refluxed for 1 hour, stopped heating, filtered , washed 3 times with 200ml of water, dried, and subjected to column chromatography to obtain 16 g of white solid with a yield of 67%.
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Abstract
The invention provides a synthetic method of benzoic acid-2-cyano-2-phenyl methyl ester. The synthetic method comprises the following steps: adding a cyaniding reagent into an ionic liquid dissolved with benzoic acid-2-bromo-2-phenyl methyl ester, then carrying out a reaction for 5-24 hours at a temperature of 100-160 DEG C, and carrying out filtering and washing after the reaction is completed, so as to obtain the benzoic acid-2-cyano-2-phenyl methyl ester, wherein the molar ratio of the benzoic acid-2-bromo-2-phenyl methyl ester to the ionic liquid to the cyaniding reagent is 1:10:(1-1.2). According to the invention, the product is synthesized through one step by taking benzoic acid-2-bromo-2-phenyl methyl ester as an initial raw material, the operation step is greatly shortened, and theyield is greatly improved. The reagents and instrument equipment required by the synthetic method are cheap and are easy to obtain, preparation cost is low, and the synthetic method is more feasiblein the specific industrial implementation.
Description
technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing benzoic acid-2-cyano-2-phenylmethyl ester. Background technique [0002] Benzoic acid-2-bromo-2-phenylmethyl ester is an important intermediate for the synthesis of mandelonitrile. By improving the synthesis method of benzoic acid-2-bromo-2-phenylmethyl ester, the efficiency of synthesizing mandelonitrile is improved. the goal that is pursued. [0003] At present, the routes for synthesizing 2-bromo-2-phenylmethyl benzoate can be roughly divided into two categories: one is benzaldehyde and benzoyl nitrile as raw materials, and the intermediate is obtained through addition and catalytic reaction. The biggest highlight of this route design is that the starting materials are cheap, which greatly reduces the synthesis cost, but the reaction steps are long and the total yield is not high; the second type of synthesis route is to use benzoyl chloride as raw m...
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