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Synthetic method of 7-(4-ethyl-1-methyl octyl)-8-hydroxyquinoline

A technology of hydroxyquinoline and methyl octyl, which is applied in the field of synthesis of 7--8-hydroxyquinoline, can solve the problems of lower product yield, low single-pass conversion rate, condensation by-products, etc., and achieve good quality and high yield. high rate effect

Inactive Publication Date: 2012-07-18
HUAIHAI INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The shortcoming of condensation method preparation 7-(4-ethyl-1-methyloctyl)-8-hydroxyquinoline is: 5-ethyl-2-nonanone and 8-hydroxyquinoline under the first step alkaline condition The condensation reaction that morphine takes place, the weak point of this step reaction is:
[0013] (1) The single-pass conversion rate is low;
[0014] (2) Under alkaline conditions, 5-ethyl-2-nonanone is prone to self-condensation to generate by-products;
[0015] (3) The condensation reaction tends to produce a large amount of tar and reduce the yield of the product

Method used

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  • Synthetic method of 7-(4-ethyl-1-methyl octyl)-8-hydroxyquinoline
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  • Synthetic method of 7-(4-ethyl-1-methyl octyl)-8-hydroxyquinoline

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Embodiment 1

[0037] Embodiment 1, a kind of synthetic method of 7-(4-ethyl-1-methyloctyl)-8-hydroxyquinoline, its steps are as follows:

[0038] (1) In a solvent, under alkali catalysis, 8-hydroxyquinoline and halogenated alkenes undergo a Williamson synthesis reaction to generate 8-[4-(5-ethyl-2-nonene)]oxyquinoline, and the reaction The temperature is 30°C, phenyl allyl ether undergoes Claisen rearrangement at this reaction temperature, and phenyl allyl ether undergoes intramolecular rearrangement to generate o-allyl 8-hydroxyquinoline, that is, to generate 7-alkenyl -8-hydroxyquinoline, which also generates 7-(4-ethyl-1-methyloctenyl)-8-hydroxyquinoline; the reaction time is 0.5 hours;

[0039] The molar ratio of the raw material halogenated olefin, 8-hydroxyquinoline and solvent is 1:0.5:2;

[0040]The halogenated olefin is 3-chloro-5-ethyl-2-nonene;

[0041] The solvent is N,N-dimethylformamide;

[0042] The catalyst base is selected from sodium hydroxide, potassium hydroxide, pota...

Embodiment 2

[0044] Embodiment 2, a kind of synthetic method of 7-(4-ethyl-1-methyloctyl)-8-hydroxyquinoline, its steps are as follows:

[0045] (1) In a solvent, under alkali catalysis, 8-hydroxyquinoline and halogenated alkenes undergo a Williamson synthesis reaction to generate 8-[4-(5-ethyl-2-nonene)]oxyquinoline, and the reaction The temperature is 180°C, phenyl allyl ether undergoes Claisen rearrangement at this reaction temperature, and phenyl allyl ether undergoes intramolecular rearrangement to generate o-allyl 8-hydroxyquinoline, that is, to generate 7-alkenyl -8-hydroxyquinoline, which also generates 7-(4-ethyl-1-methyloctenyl)-8-hydroxyquinoline; the reaction time is 12 hours;

[0046] The molar ratio of raw material halogenated olefin, 8-hydroxyquinoline and solvent is 1: 6: 12;

[0047] The halogenated olefin is 3-bromo-5-ethyl-2-nonene or 3-iodo-5-ethyl-2-nonene;

[0048] Described solvent is methanol or benzene;

[0049] The catalyst base is made by mixing an inorganic b...

Embodiment 3

[0051] Embodiment 3, a kind of synthetic method of 7-(4-ethyl-1-methyloctyl)-8-hydroxyquinoline, its steps are as follows:

[0052] (1) In a solvent, under alkali catalysis, 8-hydroxyquinoline and halogenated alkenes undergo a Williamson synthesis reaction to generate 8-[4-(5-ethyl-2-nonene)]oxyquinoline, and the reaction The temperature is 100°C, phenyl allyl ether undergoes Claisen rearrangement at this reaction temperature, and phenyl allyl ether undergoes intramolecular rearrangement to generate o-allyl 8-hydroxyquinoline, that is, to generate 7-alkenyl -8-hydroxyquinoline, which also generates 7-(4-ethyl-1-methyloctenyl)-8-hydroxyquinoline; the reaction time is 6 hours;

[0053] The molar ratio of raw material halogenated olefin, 8-hydroxyquinoline and solvent is 1:3:7;

[0054] The halogenated olefin is 3-iodo-5-ethyl-2-nonene;

[0055] Described solvent is toluene or cyclohexane;

[0056] The catalyst base is made by mixing an inorganic base with a low-carbon monohyd...

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Abstract

The invention discloses a synthetic method of 7-(4-ethyl-1-methyl octyl)-8-hydroxyquinoline. The method is characterized by comprising the following steps of: undergoing a Williamson synthetic reaction on 8-hydroxyquinoline and alkenyl halide in a solvent under the catalytic action of an alkali to generate 8-[4-(5-ethyl-2-nonylene)]oxyquinoline, performing Claisen rearrangement on ether allyl phenyl at a reaction temperature, and performing intramolecular rearrangement on ether allyl phenyl to generate 7-(4-ethyl-1-methyl octenyl)-8-hydroxyquinoline, wherein the alkenyl halide is selected from 3-chloro-5-ethyl-2-nonylene, 3-bromo-5-ethyl-2-nonylene and 3-iodine-5-ethyl-2-nonylene; and hydrogenating the 7-(4-ethyl-1-methyl octenyl)-8-hydroxyquinoline under the catalytic action of palladium / carbon to obtain a final product, i.e., 7-(4-ethyl-1-methyl octyl)-8-hydroxyquinoline. The method has the advantages of high product yield, high quality and suitability for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of 7-(4-ethyl-1-methyloctyl)-8-hydroxyquinoline. Background technique [0002] 7-(4-Ethyl-1-methyloctyl)-8-hydroxyquinoline is a highly efficient metal ion extractant, which is used as an extractant to extract gallium in the aluminum industry. In hydrometallurgy, it can be used in the content It can form chelates with some rare and precious metals in extremely low acid liquid, so as to realize the extraction of precious metals from lean ore; it can also be used to extract heavy metals from industrial sewage, or extract rare elements from seawater, etc., and has a wide range of uses. [0003] 7-alkyl-8-hydroxyquinoline has the following advantages as a metal ion extractant: the extractant has the properties of noble elements such as gallium, germanium, palladium, platinum, gold, cerium, lanthanum, zinc, nickel, cobalt and copper, etc. High selectivity, high extraction and stripping capacity, good extraction a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/26
Inventor 张珍明李润莱李树安陈庆文
Owner HUAIHAI INST OF TECH
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