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Preparation method of 5-methyl-3-cyclohexenone and application of 5-methyl-3-cyclohexenone in preparation of m-cresol

A technology of cyclohexenone and methyl, which is applied in the field of preparation, can solve problems such as harsh reaction conditions, difficult industrialization, and difficult separation, and achieve the effects of reducing processing costs, mild reaction conditions, and reducing difficulty

Active Publication Date: 2021-03-12
WANHUA CHEM GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] CN107721823A reported a method for directly preparing m-cresol by dehydrogenation of 3-methylcyclohexenone, which solved the difficult problem of separation of mixed cresols
Among them, the traditional synthesis method of 3-methylcyclohexenone, an intermediate of m-cresol, is obtained by direct oxidation of the allyl C-H bond of 3-methylcyclohexene, which has low product yield and difficult separation. Disadvantages; 3-methylcyclohexenone can also be prepared by transition metal catalyzed oxidation Heck reaction (J.Org.Chem., 2011,76,3498; Org.Lett.,2013,15,1886), but this method There are disadvantages such as expensive transition metal catalysts and harsh reaction conditions
[0009] CN101412667B adopts 1,6-heptadyne compound to prepare 2-cyclohexenone compound through hydration and intramolecular cyclization reaction, the catalyst of this synthesis technology selects precious metals such as gold or platinum, solvent has used ionic liquid, catalyst and The price of the solvent is relatively expensive, and the raw material is not easy to obtain, the yield is low, and it is difficult to industrialize

Method used

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  • Preparation method of 5-methyl-3-cyclohexenone and application of 5-methyl-3-cyclohexenone in preparation of m-cresol
  • Preparation method of 5-methyl-3-cyclohexenone and application of 5-methyl-3-cyclohexenone in preparation of m-cresol
  • Preparation method of 5-methyl-3-cyclohexenone and application of 5-methyl-3-cyclohexenone in preparation of m-cresol

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Experimental program
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preparation example Construction

[0050] (3) The preparation method of 3-butyne-2-acetate:

[0051] Dissolve 3-butyn-2-ol (5 mmol) in 10 mL of acetic anhydride, heat to reflux at 110°C for 10 h, wait for the reaction solution to cool to room temperature, rotary evaporate, and column separation to obtain 3-butyne-2 with a purity of more than 95%. - Acetate.

Embodiment 1-23

[0052] Following examples 1-23 are all used for preparing 5-methyl-3-cyclohexenone:

Embodiment 1

[0054] (1) Preparation of copper complex catalyst A

[0055] Add the metal precursor CuCl to the reaction flask 2 2H 2 O (0.02mmol) and the ligand L1 (0.025mmol) represented by the following formula, 1.0mL of anhydrous methanol was added under nitrogen protection, and stirred at room temperature for 4 hours to obtain the target product catalyst A with a molecular weight of .

[0056]

[0057] (2) dimethyl 1,3-acetonedicarboxylate (0.54mmol), 3-chloro-1-butyne (0.45mmol), and triethylamine (0.45mmol) were dissolved in 10.0mL of anhydrous methanol, and then The solution was added to the stirred catalyst A solution under the protection of nitrogen, stirred at 25° C. for 10 h (the first stage), and then stirred at 120° C. for 8 hours (the second stage). After the reaction was completed, rotary evaporation under reduced pressure and column separation gave the product 5-methyl-3-cyclohexenone with a yield of 95.2%.

[0058] 1 H NMR (CDCl 3 ,400MHz):δ6.15(m,1H),5.66(m,1H),3.1...

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Abstract

The invention discloses a preparation method of 5-methyl-3-cyclohexenone and application thereof in preparation of m-cresol, and the preparation method comprises the following step: in the presence orabsence of an alkali additive, carrying out [3 + 3] cycloaddition reaction on a 1, 3-acetone dicarboxylic acid diester compound and a propargyl compound to generate the 5-methyl-3-cyclohexenone shownas a formula III. The method has the advantages of simple synthesis route, mild reaction conditions, high yield and the like. The invention discloses a method for preparing m-cresol from 5-methyl-3-cyclohexenone The m-cresol is prepared from 5-methyl-3-cyclohexenone through a dehydrogenation reaction. The m-cresol prepared by the method does not produce o-cresol and p-cresol as byproducts, and the problem of separation of mixed cresol is effectively avoided.

Description

technical field [0001] The invention relates to a preparation method, in particular to a preparation method of 5-methyl-3-cyclohexenone and its application in the preparation of m-cresol. Background technique [0002] m-cresol is an important intermediate of pharmaceuticals, spices and nutritional chemicals. It can be used to produce trimethylhydroquinone, a synthetic intermediate of vitamin E, and thymol, a pesticide intermediate m-phenoxybenzaldehyde, and an antioxidant 6-tert-butyl m-cresol. [0003] m-cresol can be extracted from coking kerosene and petroleum residue, but the output is small and cannot meet the downstream demand. At present, the main methods of industrial production of m-cresol include toluene sulfonation alkali fusion method, o-chlorotoluene hydrolysis method, arylamine diazo method and isopropyl toluene method. Among them, the toluene sulfonation alkali fusion method has a long process route, uses a large amount of strong acid and strong alkali, caus...

Claims

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Application Information

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IPC IPC(8): C07C45/69C07C49/603B01J31/18C07C37/07C07C39/07
CPCC07C45/69B01J31/1815C07C37/07C07C2601/16B01J2531/16B01J2531/0241B01J2231/328C07C49/603C07C39/07
Inventor 姜鹏张德旸沈稳刘连才孔令晓张永振黎源
Owner WANHUA CHEM GRP
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