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Synthesis method of metal salt catalyzed alpha-diketone compound

A synthesis method and metal salt technology, applied in the preparation of organic compounds, separation/purification of carbonyl compounds, preparation of carbonyl compounds, etc., can solve the problems of high reaction temperature, complicated operation, deep oxidation, etc., and achieve high yield, The synthesis method is simple and the conditions are mild

Active Publication Date: 2020-10-23
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are mainly three traditional methods for preparing α-diketones: the nucleophilic addition-elimination reaction method is flexible, but the operation is more complicated, and the reaction requires low temperature, which is generally used to synthesize more complex α-diketones; the coupling method is simple , the conditions are mild, but it has just been developed and is still immature, and some coupling reaction products are more complicated; the oxidation method is simple to operate, but the oxidant is generally poisonous, and it is easy to cause deep oxidation, and the metal oxidant is expensive, and the reaction temperature is high

Method used

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  • Synthesis method of metal salt catalyzed alpha-diketone compound
  • Synthesis method of metal salt catalyzed alpha-diketone compound
  • Synthesis method of metal salt catalyzed alpha-diketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of 6-methyl-5-heptene-3,4-dione

[0026]

[0027] In a thoroughly dry Schlenk reaction tube, add 0.0207g (0.1mmol, 2mol%) silver perchlorate (AgClO 4 ), 0.4206g (5mmol) 2-methyl-3-butyn-2-ol, 3.2535g (25mmol) propionic anhydride. Then the system was placed at 25°C under magnetic stirring for 12 hours. After the reaction was completed, the acid was removed with saturated sodium bicarbonate, and the crude product was separated by column chromatography. Pure n-hexane to n-hexane:petroleum ether=1 :1 is the eluent purification to obtain the target product 6-methyl-5-heptene-3,4-dione with a yield of 90%.

[0028] figure 1 For 6-methyl-5-heptene-3,4-dione in this embodiment 1 H NMR spectrum, figure 2 For 6-methyl-5-heptene-3,4-dione in this embodiment 13 C NMR spectrum.

[0029] from figure 1 It can be seen in: 1 H NMR (500MHz, Chloroform-d) δ7.25(m, 1H), 2.43(q, J=7.6Hz, 2H), 1.85(d, J=2.1Hz, 6H), 1.19(t, J=7.6Hz ,3H). This is consistent with the com...

Embodiment 2

[0033] Synthesis of 6-methyl-5-heptene-3,4-dione

[0034]

[0035] In a thoroughly dry Schlenk reaction tube, add 0.0207g (0.1mmol, 2mol%) silver perchlorate (AgClO 4 ), 0.4206g (5mmol) 2-methyl-3-butyn-2-ol, 3.2535g (25mmol) propionic anhydride. Then the system was placed at 25°C under magnetic stirring for 6 hours. After the reaction was completed, the acid was removed with saturated sodium bicarbonate, and the crude product was separated by column chromatography. Pure n-hexane to n-hexane:petroleum ether=1 :1 is the eluent purification to obtain the target product 6-methyl-5-heptene-3,4-dione with a yield of 88%.

Embodiment 3

[0037] Synthesis of 6-methyl-5-heptene-3,4-dione

[0038]

[0039] In a thoroughly dry Schlenk reaction tube, add 0.0104g (0.05mmol, 1mol%) silver perchlorate (AgClO 4 ), 0.4206g (5mmol) 2-methyl-3-butyn-2-ol, 0.6507g (5mmol) propionic anhydride. Then the system was placed at 25°C under magnetic stirring for 12 hours. After the reaction was completed, the acid was removed with saturated sodium bicarbonate, and the crude product was separated by column chromatography. Pure n-hexane to n-hexane:petroleum ether=1 :1 is the eluent purification to obtain the target product 6-methyl-5-heptene-3,4-dione with a yield of 61%.

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Abstract

The invention relates to the technical field of catalysis and organic chemistry, in particular to a synthesis method of a metal salt catalyzed alpha-diketone compound. According to the method, propargyl alcohol and anhydride are adopted as raw materials and react under the catalytic action of metal salt to obtain the compound with the olefine diketone structure, the structural formula is shown inthe specification, R1 and R2 are selected from any one of methyl, ethyl, cyclohexyl and phenyl, and R3 is selected from any one of methyl, ethyl, propyl, isopropyl, isobutyl and n-heptyl. The synthesis method is simple and mild in condition, the alpha-diketone product synthesized by the propargyl alcohol and anhydride one-pot method is used for the first time, the raw materials are cheap and easyto obtain, and the yield is very high.

Description

technical field [0001] The invention relates to the technical fields of catalysis and organic chemistry, in particular to a method for synthesizing α-diketone compounds catalyzed by metal salts. Background technique [0002] α-diketone is a kind of active bifunctional compound, its structure is 1,2-dicarbonyl structure, and there are many reactive centers, it is an important intermediate in organic synthesis, used for the synthesis of heterocyclic compounds and heterocyclic metal complexes , can be used as a chromogen in analytical chemistry. α-diketone is also widely found in many natural products, and has a creamy flavor at low concentrations, so it is used as a flavor enhancer for margarine and candy, and has a huge demand in the fragrance market. α-diketones are also used in drugs and drug analogs, and such structures are commonly found in optical materials and dyes. In daily life, α-diketone can also be used as a deodorant, which can be used in food, toothpaste and ai...

Claims

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Application Information

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IPC IPC(8): C07C45/00C07C45/79C07C49/203C07C49/21C07C49/217
CPCC07C45/00C07C45/79C07C2601/14C07C49/203C07C49/21C07C49/217Y02P20/584
Inventor 原晔卜超沙南
Owner WUHAN UNIV OF TECH
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