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Synthetic method of methyl ketone compound

A synthesis method and technology for methyl ketones are applied in the field of synthesis of methyl ketone compounds, can solve problems such as application limitations, and achieve the effects of simple operation, high conversion rate and mild reaction conditions

Pending Publication Date: 2020-05-19
DALIAN CHEMPHY CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the Kucherov reaction and its improved method are greatly limited in application.

Method used

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  • Synthetic method of methyl ketone compound
  • Synthetic method of methyl ketone compound
  • Synthetic method of methyl ketone compound

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preparation example Construction

[0027] The invention provides a kind of synthetic method of methyl ketone compound, comprises the following steps:

[0028] Mixing a terminal alkyne having a structure shown in formula I, an organic solvent, an acid and water for a hydration reaction to obtain a methyl ketone compound;

[0029]

[0030] In formula I: R 1 is hydrocarbyl, substituted hydrocarbyl, hydrocarbyl formyl, aryl, aryl formyl, substituted aryl, substituted aryl formyl, heterocycle or heterocyclic formyl, R 2 and R 3 are independently hydrocarbyl, substituted hydrocarbyl or cyclohydrocarbyl.

[0031] The present invention has no special requirements on the source of the terminal alkyne having the structure shown in formula I, and it can be prepared by using commercially available products or by methods well known to those skilled in the art.

[0032] The reaction equation of the present invention's synthetic methyl ketone compound is shown in formula a:

[0033]

[0034] In the present invention...

Embodiment 1

[0047] Embodiment 1: the synthesis of 3-phenyl-3-methylbutan-2-one

[0048] Reaction formula:

[0049]

[0050] Reaction raw materials and consumption are shown in Table 1:

[0051] Table 1 Reaction raw materials and consumption

[0052]

[0053] Dissolve 144.2 g of (2-methylbutyl-3-yn-2-yl)benzene in 720 g of tetrahydrofuran, add 110.6 g of 33 wt% hydrochloric acid solution and 21.6 g of water, raise the temperature to 40° C., and stir for 6 hours. After all the raw materials were converted, the reaction mixture was cooled to room temperature, washed with 500 mL of aqueous sodium bicarbonate solution and 500 mL of brine, separated the organic phase, and concentrated under reduced pressure to remove the solvent. The obtained residue was distilled under reduced pressure to obtain pure 3-phenyl-3-methyl-butan-2-one.

[0054] 156.2 g (0.96 mol) of the product were obtained, yield: 96.4%, gas chromatography purity: 99.2%.

Embodiment 2

[0055]Example 2: Synthesis of 3-cyclohexyl-3-methylbutan-2-one

[0056] Reaction formula:

[0057]

[0058] The reaction raw materials and consumption are shown in Table 2:

[0059] Table 2 Reaction raw materials and consumption

[0060]

[0061]

[0062] Dissolve 150.1 g of (2-methylbutyl-3-yn-2-yl)cyclohexane in 720 g of tetrahydrofuran, add 98 g of 50 wt% sulfuric acid solution and 21.6 g of water, raise the temperature to 30°C, and stir for 7.5 hours , after all the raw materials were converted, the reaction mixture was cooled to room temperature, washed with 500 mL of aqueous sodium bicarbonate solution and 500 mL of brine, separated the organic phase, and concentrated under reduced pressure to remove the solvent. The obtained residue was distilled under reduced pressure to obtain pure 3-cyclohexyl-3-methylbutan-2-one.

[0063] 160 g (0.95 mol) of the product were obtained, the yield: 95%, and the purity by gas chromatography: 98.5%.

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Abstract

The invention relates to the technical field of organic synthesis, and provides a synthesis method for a methyl ketone compound. The synthesis method comprises the following steps: mixing terminal alkyne, an organic solvent, an acid and water, and carrying out a hydration reaction to obtain a methyl ketone compound. According to the synthetic method provided by the invention, the use a catalyst containing metal ions and an oxidizing agent can be avoided, the raw materials are directly subjected to the hydration reaction in the presence of acid and water, and the complicated operation of removing metal ions is avoided in the post-treatment process of the produced methyl ketone compound; the method provided by the invention is high in raw material conversion rate and relatively high in product yield and product purity; the synthesis reaction process is simple and convenient to operate, green and environment-friendly, and suitable for large-scale industrial production; the synthetic method provided by the invention is mild in reaction conditions and easy to control. Results of an embodiment of the invention show that when the method is used for preparing the methyl ketone compound, yield can reach 96.4%, and product purity reaches 99.2%.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing methyl ketone compounds. Background technique [0002] Methyl ketones are commonly used intermediates in organic synthesis, and are often used in fine organic synthesis fields such as pharmaceuticals, pesticides, and fine chemical intermediates, and have broad application space. Many organic chemical products use methyl ketones as raw materials to prepare the desired target products through halogenation, condensation, ring formation and other reactions. [0003] Conventional methods for the preparation of methyl ketones include olefin oxidation, alkyne hydration, and the like. [0004] Olefin oxidation is usually prepared by basic oxidation of potassium permanganate, and the reaction formula is as follows: [0005] [0006] Since potassium permanganate reacts to generate manganese dioxide solid waste, which has a great impact on the enviro...

Claims

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Application Information

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IPC IPC(8): C07C45/26C07C49/11C07C49/213C07C49/76
CPCC07C45/26C07C2601/14C07C49/213C07C49/11C07C49/76
Inventor 马建华赵宏马晓爽徐海珍
Owner DALIAN CHEMPHY CHEM
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