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Method for directly converting aldehyde or alcohol into carboxylic acid

A transformative and direct technology, applied in the direction of organic chemical methods, chemical instruments and methods, carboxylate preparation, etc., can solve the problems of uneconomical convenience, metal residues, etc., and achieve environmental friendliness, high catalytic efficiency, and convenient and simple operation Effect

Inactive Publication Date: 2018-07-24
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] It can be seen that most of the existing technologies use metal catalysts and equivalent or even excess oxidants, thus failing to avoid the problems of metal residues and uneconomical convenience in synthetic medicinal chemistry

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: N-hexanoic acid Synthesis

[0018] Add 5mol% NHPI into a 25mL Schlenk reaction tube, dry it in vacuum for 15 minutes, blow in oxygen, add 2mL of acetonitrile and 1.0 equivalent of n-hexanal in sequence under an oxygen atmosphere, connect an oxygen bulb, add a glass stopper to the reaction tube and put In an oil bath, react at 30°C for 3h. After the reaction was completed, it was concentrated under reduced pressure, separated by column chromatography, and the eluent was petroleum ether / ethyl acetate / dichloromethane (v:v:v=2:1:1) to obtain n-hexanoic acid. Yield>99%, colorless liquid; 1 HNMR (400MHz, CDCl 3 )δ2.36(t,J=7.2Hz,2H),1.65–1.61(m,2H),1.34–1.30(m,4H),0.91–0.88(m,3H). 13 C NMR (100MHz, CDCl 3 )δ180.67, 34.07, 31.18, 24.33, 22.26, 13.81.

Embodiment 2

[0019] Example 2: N-heptanoic acid Synthesis

[0020] Add 5mol% NHPI into a 25mL Schlenk reaction tube, dry it in vacuum for 15 minutes, blow in oxygen, add 2mL of acetonitrile and 1.0 equivalent of n-heptanal in sequence under an oxygen atmosphere, connect an oxygen bulb, add a glass stopper to the reaction tube and put In an oil bath, react at 30°C for 3h. After the reaction was completed, it was concentrated under reduced pressure, separated by column chromatography, and the eluent was petroleum ether / ethyl acetate / dichloromethane (v:v:v=5:1:1) to obtain n-heptanoic acid. Yield 93%, colorless liquid; 1 HNMR (400MHz, CDCl 3 )δ2.36(t, J=7.6Hz, 2H), 1.64(t, J=7.2Hz, 2H), 1.25–1.35(m, 6H), 0.88(t, J=6.8Hz, 3H). 13 CNMR (100MHz, CDCl 3 )δ180.91, 34.46, 31.75, 29.05, 24.96, 22.78, 14.32.

Embodiment 3

[0021] Example 3: Lauric acid n-C 11 h 23 CHO→n-C11 h 23 Synthesis of COOH

[0022] Add 5mol% NHPI into a 25mL Schlenk reaction tube, dry it in vacuum for 15 minutes, blow in oxygen, add 2mL of acetonitrile and 1.0 equivalent of laurylaldehyde in an oxygen atmosphere, connect an oxygen bulb, add a glass stopper to the reaction tube, and put In an oil bath, react at 30°C for 3h. After the reaction was completed, it was concentrated under reduced pressure, separated by column chromatography, and the eluent was petroleum ether / ethyl acetate / dichloromethane (v:v:v=5:1:1) to obtain lauric acid. Yield 90%, solid; 1 H NMR (400MHz, CDCl 3 )δ2.36(t, J=7.6Hz, 2H), 1.66–1.59(m, 2H), 1.29(s, 16H), 0.895(t, J=6.4Hz, 3H). 13 C NMR (100MHz, CDCl 3 )δ180.73, 34.43, 32.25, 29.94, 29.77, 29.67, 29.57, 29.40, 25.01, 23.02, 14.44.

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PUM

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Abstract

The invention discloses a method for directly converting aldehyde or alcohol into carboxylic acid. The method is characterized by oxidizing CH2OH and CHO under catalysis of N-hydroxyimide compounds orunder combined catalysis of N-hydroxyimide compounds and nitrite compounds in a pure oxygen environment, and directly converting CH2OH and CHO into a carboxylic acid compound. According to the method, the oxygen is used as an oxidant; no metal catalyst is added; the method is environmentally friendly and is high in catalysis efficiency and convenient and simple to operate; the method is differentfrom the previous metal catalysis system and compound catalysis system; the residues of transition metals are caused when the transition metals are used in the existing metal catalysis system process; the method adopts a non-metal catalysis system which is green and environmentally friendly, so that the problem of the residues of the metals is avoided; a novel method is provided for solving the problem of the residues of the transition metals during drug synthesis.

Description

technical field [0001] The present invention belongs to oxidation catalysis CH 2 The technical field of forming carboxylic acid compounds from OH and CHO, specifically relates to a method for directly converting alcohols or aldehydes into carboxylic acids through oxidation. Background technique [0002] Carboxylic acids are widely found in nature and play a very important role in human's daily life. Among the drugs approved by the FDA, a large number of drugs contain carboxylic acid structures. For example, ibuprofen for rheumatism and rheumatoid arthritis, ofloxacin for acute and chronic infections of the respiratory tract, throat, tonsils and other parts caused by Gram-negative bacteria, captopril, gemfi Betsy, mefenamic acid, etc. Carboxylic acids are also commonly used as intermediates in the synthesis of esters, amides and nitriles. Esters, amides, and nitriles are also present in large quantities in common drug molecules. For example, diclofenac sodium, piroxicam,...

Claims

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Application Information

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IPC IPC(8): C07B41/08C07C51/235C07C53/126C07C53/124C07C53/128C07C61/06C07C61/08C07C53/134C07C53/19C07C59/84C07C57/30C07C57/32C07C57/40C07C65/21C07C63/36C07C269/06C07C271/22C07D209/18
CPCC07B41/08C07C51/235C07C269/06C07D209/18C07C53/126C07C53/124C07C53/128C07C61/06C07C61/08C07C53/134C07C53/19C07C59/84C07C57/30C07C57/32C07C57/40C07C65/21C07C63/36C07C271/22
Inventor 康彦彪代鹏飞
Owner UNIV OF SCI & TECH OF CHINA
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