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A kind of synthetic method of carboxylic acid or ester compound

A technology of ester compound and synthesis method, which is applied in the field of synthesis of carboxylic acid or ester compound, can solve the problems of difficult separation, non-recycling, large amount of condensing agent, etc., achieve mild reaction conditions, save production cost, and simple post-treatment Effect

Active Publication Date: 2016-12-07
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One is the catalysis of condensation agents such as excess dicyclohexylsuccinimide (DCC), diisopropylsuccinimide (DIC), 1-hydroxy-benzo-triazole (HOBT) Under this method, the carboxylic acid generates an active ester intermediate, reacts with alcohol to generate an ester, and produces an equal amount of difficult-to-separate urea compounds (DCU, DIU, etc.); the significant disadvantage of this method is that the amount of condensing agent is large, the price is expensive, and it cannot be recycled. , converted into urea compounds that are difficult to separate after the reaction
Another method is that carboxylic acid reacts with thionyl chloride to generate acid chloride, and then reacts with alcohol to generate ester in the presence of acid-binding agent; the disadvantage of this method is that gases such as hydrogen chloride and sulfur dioxide will , seriously corrode and pollute the environment; at the same time, since the acid chloride has to be purified by distillation, the operation steps are increased, and the total production cost is high

Method used

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  • A kind of synthetic method of carboxylic acid or ester compound
  • A kind of synthetic method of carboxylic acid or ester compound
  • A kind of synthetic method of carboxylic acid or ester compound

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Example 1: Preparation of methyl benzoate (III-1)

[0027] The reaction formula is as follows:

[0028]

[0029] Under air atmosphere, add 0.005g (2.5‰mmol Ru) Ru / C catalyst to the reaction flask, then add 10mL methanol (II-1), and then add 117μL (1mmol) benzylacetonitrile (I-1) under stirring. Add to the reaction flask, keep the temperature at about 30°C, stir and react for 37 hours, monitor the reaction, and the raw material (I-1) has basically reacted completely. After the reaction is completed, filter, wash the filter residue twice with methanol, combine the filtrate, dry, concentrate, and thin-layer chromatography (ethyl acetate / petroleum ether = 1 / 10) to obtain methyl benzoate represented by formula (III-1) The ester is 0.125g, the yield is 92.2%, and the purity is 98%. The structure of compound formula (III-1) is characterized as follows:

[0030] 1 H NMR(600MHz, CDCl 3 )δ8.05-8.03(m,2H),7.56-7.54(m,1H),7.44-7.43(m,2H),3.88(s,3H); GC-MS(EI): m / z 136[M + ].

Embodiment 2

[0031] Example 2: Preparation of methyl benzoate (III-1)

[0032] Under air atmosphere, add 0.01g (5‰mmol Ru) Ru / C catalyst to the reaction flask, then add 10mL methanol (II-1), and then add 117μL (1mmol) benzylacetonitrile (I-1) under stirring. Add to the reaction flask, keep the temperature at about 30°C, stir and react for 26 hours, monitor the reaction, and the raw material (I-1) basically reacts completely. After the reaction is completed, filter, wash the filter residue twice with methanol, combine the filtrate, dry, concentrate, and thin-layer chromatography (ethyl acetate / petroleum ether = 1 / 10) to obtain methyl benzoate represented by formula (III-1) The ester is 0.126 g, the yield is 93%, and the purity is 98%.

Embodiment 3

[0033] Example 3: Preparation of methyl benzoate (III-1)

[0034] Under air atmosphere, add 0.02g (10‰mmol Ru) Ru / C catalyst to the reaction flask, then add 10mL methanol (II-1), and then add 117μL (1mmol) benzylacetonitrile (I-1) under stirring. Add to the reaction flask, keep the temperature at about 30°C, stir and react for 20 hours, monitor the reaction, and the raw material (I-1) basically reacts completely. After the reaction is completed, filter, wash the filter residue twice with methanol, combine the filtrate, dry, concentrate, and thin-layer chromatography (ethyl acetate / petroleum ether = 1 / 10) to obtain methyl benzoate represented by formula (III-1) The ester is 0.130 g, the yield is 94.5%, and the purity is 98%.

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Abstract

The invention discloses a synthesis method for a carboxylic acid or ester compound shown as formula (III). The method includes the steps of: in the air atmosphere, taking substituted acetonitrile shown as formula (I) and a compound shown as formula (II) as the raw materials, taking Ru / C as the catalyst, and carrying out reaction in a solvent to generate the carboxylic acid or ester compound shown as formula (III). The solvent is selected from one of the following: the compound itself shown as formula (II) and dimethylsulfoxide. The invention provides a new synthetic route, the operation is simple, the aftertreatment is convenient, the product has high yield and high purity, especially the catalyst and the solvent can be used repeatedly, and air is used as the oxidizing agent. The method provided by the invention not only saves the cost of production, but also reflects environmental friendliness, and is very suitable for industrial mass production. (formula I, formula II, formula III).

Description

Technical field [0001] The invention relates to a method for synthesizing a carboxylic acid or ester compound represented by formula (III); [0002] Background technique [0003] Transition metals occupy an extremely important position in the field of catalysis, and many palladium and rhodium catalysts have been industrially applied. The development of ruthenium catalysts lags behind that of palladium and rhodium catalysts due to the difficulty of matching with substrates. Until the 1980s, it has been reported that the synthesis methods using ruthenium catalysts were limited to a few, such as oxidation reactions, hydrogenation reactions, and hydrogen transfer reactions. Due to the 4d75s1 electronic structure of ruthenium, it has the most oxidation state among all the elements in the periodic table, and each electronic structure has a variety of geometric structures, which provides a good basis for the synthesis of diverse ruthenium complexes. The ligands used in ruthenium compl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B41/12C07C67/22C07C69/78C07C69/76C07D235/24C07D213/80C07D213/803C07D277/68C07C63/06C07C51/08
Inventor 王宇光朱冰春吴中礼李钦
Owner ZHEJIANG UNIV OF TECH
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