Method for oxidizing alcohol into aldehyde, ketone or carboxylic acid

A carboxylic acid and oxidizing technology, which is applied in the direction of organic chemical methods, chemical instruments and methods, and carboxylate preparation, can solve the problems of severe reaction process and troubles, and achieve good repeatability, easy operation, and easy reaction conditions Effect

Active Publication Date: 2013-02-13
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These processes also use a large amount of highly toxic reagents, and the reaction process is violent, which has been the main reason that has long plagued the practical application of this type of oxidation reaction.

Method used

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  • Method for oxidizing alcohol into aldehyde, ketone or carboxylic acid
  • Method for oxidizing alcohol into aldehyde, ketone or carboxylic acid
  • Method for oxidizing alcohol into aldehyde, ketone or carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Add p-methoxybenzyl alcohol (1mmol), potassium tert-butoxide (0.1mmol) and imidazolium salt (9) (10μmol) into the reaction tube, vacuumize the system and flush it with air, add 10mL of toluene as a solvent, add a few capsules Molecular sieves and tetra-n-butylammonium iodide (0.05 mmol) were stirred at room temperature for 12 hours to obtain the product p-methoxybenzaldehyde with a yield of 95%.

[0037] 1 H NMR (300MHz, CDCl 3 )δ9.82(s,1H),7.78(d,J=8.7Hz,1H),6.94(d,J=8.6Hz,2H),3.82(s,3H);ESI-MS[M+Na]m / z159.0.

Embodiment 2

[0039] Add p-4-hydroxy-3-methoxybenzyl alcohol (1mmol), triethylamine (1.5mmol), metal nitrogen heterocyclic carbene complex [Ag(25) 2 ] + BF 4 - (20μmol), pure oxygen after the system was evacuated, added 8mL of anhydrous dichloromethane as a solvent, added 25mg of anhydrous sodium sulfate and tetra-n-butylphosphonium chloride (15μmol) and stirred at 45°C for 24 hours to obtain 4-hydroxy-3 -Methoxybenzaldehyde (i.e. vanillin), 92% yield.

[0040] 1 H NMR (300MHz, CDCl 3 )δ9.77(s,1H),7.56–7.30(m,2H),7.00(d,J=8.5Hz,1H),6.81(s,1H),3.89(s,3H); ESI-MS[M ]m / z152.0.

Embodiment 3

[0042] Add geraniol (1mmol), potassium hydroxide (2mmol), iron powder, imidazolium salt (12) (0.02mmol) and 30mg calcium chloride into the reaction tube, add 13mL DME as solvent and tetraethylammonium chloride (50μmol) , stirred at room temperature for 6 hours to obtain the product geranial (ie citral), with a yield of 99%.

[0043] 1 H NMR (300MHz, CDCl 3 )δ9.91(dd,J=30.1,8.2Hz,1H),5.84(d,J=8.0Hz,1H),5.05(d,J=7.9Hz,1H),2.56(t,J=7.4Hz, 1H),2.37–2.08(m,4H),1.95(s,2H),1.65(s,3H),1.57(d,J=4.9Hz,3H); EI-MS[M+H]m / z153. 1.

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Abstract

The invention discloses a method for oxidizing alcohol into aldehyde, ketone or carboxylic acid. The method utilizes a metal nitrogen heterocyclic carbine compound as the catalytic agent and oxygen in air as the oxidizing agent. The method comprises the steps of selectively oxidizing alcohol compounds into the aldehyde or the ketone efficiently and gently; and oxidizing alpha-hydrogen-free primary alcohol into corresponding carboxylic acid compounds efficiently under the heating condition.

Description

technical field [0001] The present invention belongs to a novel high-efficiency, specific and green method for preparing corresponding aldehydes, ketones or carboxylic acids respectively from alcohol compounds. Specifically, a metal nitrogen heterocyclic carbene or its imidazolium salt precursor is used as a catalyst, and the alcohol compounds are Substrate, oxidizing gas is an oxidant, and the method of preparing aldehyde, ketone or carboxylic acid with high yield by changing different reaction conditions under the participation of alkali. Background technique [0002] Oxidation of alcohols is an important class of organic reactions. Among them, the primary alcohol (RCH 2 OH) can be oxidized to aldehydes (RCHO) or carboxylic acids (RCO 2 H); and secondary alcohol (R 1 R 2 CHOH) is usually oxidized to a ketone (R 1 R 2 C=O) form; tertiary alcohol (R 1 R 2 R 3 COH) is generally difficult to undergo oxidation reactions. The direct oxidation of primary alcohols to car...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/06C07B41/08C07C45/38C07C47/575C07C47/58C07C47/21C07C49/78C07C47/232C07C47/565C07D213/48C07D333/22C07C49/04C07C49/675C07D333/40C07C51/255C07C63/70C07C65/21
Inventor 姜标韩磊
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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