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Copper salt catalyzing system

A catalytic system, copper salt technology, applied in organic chemistry, chemical instruments and methods, preparation of organic compounds, etc., can solve the problem of increasing the difficulty and cost of industrial production operations, affecting the application of methyl benzoate compounds, and precious metal catalyst residues, etc. problem, to achieve the effect of low catalyst dosage, mild conditions and low cost

Inactive Publication Date: 2013-07-10
HUNAN ZHUIYI INTELLIGENT MACHINERY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But, we can see that there are following problems in the prior art by benzyl alcohol making methyl benzoate compound from above: 1. basically all use precious metal as catalyst, and production cost is expensive; 2. reaction basically all carries out in the atmosphere of oxygen, greatly Increased operational difficulty and cost of industrial production; ③ precious metal catalysts are easy to remain in the product, which affects the application of methyl benzoate compounds in occasions such as drug synthesis

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment one: the preparation of methyl benzoate

[0021] Benzyl alcohol (0.5 mmol), 8-hydroxyquinoline copper (0.05 mmol), tetrabutylammonium iodide (0.1 mmol), potassium phosphate (1 mmol), and dimethyl sulfoxide (2 ml), add di-tert-butyl peroxide (1.5 mmol) with a micro-injector, seal the system and heat it in an oil bath at 100°C for about 2 hours. (Petroleum ether (60°C) was used as the eluent) to obtain the esterification product methyl benzoate with a yield of 92%. Its NMR data are: 1 H NMR (400 MHz, CDCl 3 ) ( δ , ppm) 8.04 (d, J = 8.0 Hz, 2H), 7.56 (d, J = 8.0 Hz, 1H), 7.44 (dd, J 1 = J 2 = 7.5 Hz, 2H), 3.92 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) ( δ , ppm ) 167.0, 132.7, 130.0, 129.4, 128.2, 51.9; mass spectrum data: MS: Anal. Calcd. For C 8 h 9 o 2 : 137.1, Found: 137.1 (M+1) + . The above data prove that the obtained compound is indeed the compound methyl benzoate.

Embodiment 2

[0022] Embodiment two: the preparation of methyl benzoate

[0023] Benzyl alcohol (0.5 mmol), elemental copper (0.04 mmol), tetrabutylammonium iodide (0.1 mmol), potassium phosphate (1 mmol), and dimethyl sulfoxide (2 ml) were sequentially placed in a Schlenk test tube, and the Add di-tert-butyl peroxide (1.5 mmol) into the micro-injector, seal the system and heat it in an oil bath at 100°C for about 2 hours. The esterification product methyl benzoate can be obtained by using petroleum ether (90°C) with a yield of 90%. Its NMR data are: 1 H NMR (400 MHz, CDCl 3 ) ( δ , ppm) 8.04 (d, J = 8.0 Hz, 2H), 7.56 (d, J = 8.0 Hz, 1H), 7.44 (dd, J 1 = J 2 = 7.5 Hz, 2H), 3.92 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) ( δ, ppm ) 167.0, 132.7, 130.0, 129.4, 128.2, 51.9; MS data: MS: Anal. Calcd. For C 8 h 9 o 2 : 137.1, Found: 137.1 (M+1) + . The above data prove that the obtained compound is indeed the compound methyl benzoate.

Embodiment 3

[0024] Embodiment three: the preparation of methyl p-methoxybenzoate

[0025] In a Schlenk test tube, add p-methoxybenzyl alcohol (0.5 mmol), 8-hydroxyquinoline copper (0.06 mmol), tetrabutylammonium iodide (0.1 mmol), potassium phosphate (1 mmol), and dimethyl Sulfoxide (2 ml), add di-tert-butyl peroxide (0.9 mmol) with a micro-injector, seal the system and heat it in an oil bath at 100°C for about 2 hours, distill off the solvent after the reaction, concentrate and pass Column chromatography (petroleum ether (70°C) as the eluent) was used to obtain the esterified product methyl p-methoxybenzoate with a yield of 98%. Its NMR data are: 1 H NMR (400 MHz, CDCl 3 ) ( δ , ppm) 7.99 (d, J =8.0 Hz, 2H), 6.91 (d, J =8.0 Hz, 2H), 3.88 (s, 3H), 3.85 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) ( δ , ppm) 167.0, 163.5, 131.8, 122.8, 113.8, 55.6, 52.0; MS data: MS: Anal. Calcd. For C 9 h 11 o 3 : 167.1, Found: 167.1 (M+1) + . The above data prove that the obtained compound is i...

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Abstract

The invention discloses a copper salt catalyzing system. The copper salt catalyzing system is used for catalyzing esterification reaction to prepare a methyl benzoate compound. The copper salt catalyzing system is composed of a copper salt, an oxidant and an alkali, wherein the mol ratio of the copper salt to the oxidant is 1: 15 to 40; the copper salt is selected from one or a mixture of more than one of 8-hydroxyquinoline copper, cupric acetate monohydrate, copper acetylacetonate, cuprous bromide, anhydrous cupric sulfate, copper fluoride dihydrate and pure copper; and the oxidant is one of tert-butyl hydroperoxide, di-tert-butyl oxide or dicumyl peroxide. The newly developed copper salt catalyzing system for benzyl alcohol esterification reaction greatly reduces the reaction cost, the raw materials are simple and easy to gain, the system is in a wide applicable scope of substrates, the yield is up to 99%, the reaction is carried out in the air atmosphere, the operation is simple, and the chemoselectivity is high; and the copper salt catalyzing system is environmentally friendly, has no three-waste discharge, meets green chemistry requirements, and is also beneficial for industrial application.

Description

technical field [0001] The invention belongs to the field of catalysts, and in particular relates to a copper salt catalyst system without the participation of noble metals. The catalyst system can catalyze an esterification reaction to prepare methyl benzoate compounds. Background technique [0002] The compound generated by the dehydration of carboxylic acid (or oxyacid) and methanol is called methyl ester compound, among which methyl benzoate compound is a very useful chemical structural unit, which is widely used in industrial and agricultural production. great application. For example, methyl p-hydroxybenzoate is mainly used as a bactericidal preservative in organic synthesis, food, cosmetics, and medicine, and also as a feed preservative. Because it has a phenolic hydroxyl structure, its antibacterial performance is stronger than that of benzoic acid and sorbic acid. ; methyl 4-[3-(dibutylamino)propoxy]benzoate is an important intermediate in the synthesis of dronedar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/12C07C67/40C07C69/78C07C69/92C07C69/76C07C205/58C07C205/57C07C205/59C07C201/12C07C253/30C07C255/57C07D233/64
Inventor 毛金成朱研晏宏陆林华荣光伟刘德福
Owner HUNAN ZHUIYI INTELLIGENT MACHINERY
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