Preparation of 3-methylcy-clopentadecanone

A kind of methyl cyclopentadecanone, said technology, is applied in the preparation field of 3-methyl cyclopentadecanone

Active Publication Date: 2008-11-05
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the method for preparing muskone disclosed in "Fine Chemical Industry" 2006, 23(5): 463-465, although the yield of hexadecane-2,15 has been increased to 78.6%, the inventor of the present invention think there is still room for improvement

Method used

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  • Preparation of 3-methylcy-clopentadecanone
  • Preparation of 3-methylcy-clopentadecanone
  • Preparation of 3-methylcy-clopentadecanone

Examples

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preparation example Construction

[0026] The said method of preparing 3-methylcyclopentadecone of the present invention, it comprises the steps:

[0027] (1) In the presence of an inorganic base and a compound represented by formula I, place 1,10-dibromodecane, ethyl acetoacetate and an aprotic polar solvent in a reactor at a temperature of 30°C to 150°C , the pressure is under the condition of 50kPa~1000kPa, after reacting for 0.5-30 hours, after separation (comprising the compound shown in formula I and steaming the aprotic polar solvent used), the solid is separated, and the solid is treated with alkali metal hydroxide Hydrolyze with dilute alcohol solution, filter and recrystallize to get hexadecanedione-(2,15).

[0028]Wherein: the molar ratio of 1,10-dibromodecane and ethyl acetoacetate is (1~20): 1, preferably (5~15): 1; the consumption of the compound shown in formula I is used 1,10- 2wt%~80wt% (preferably 5wt%~60wt%) of dibromodecane weight; Said inorganic base is selected from: the carbonate of alka...

Embodiment 1

[0036] (1) In a 250ml flask, add 100ml toluene, 12g (0.04mol) 1,10-dibromodecane, 4g of anhydrous potassium carbonate, 1g of dodecyltrimethylammonium chloride, 50g of ethyl acetoacetate, and use Adjust the transformer to heat it to reflux (82°C) and react for 15 hours. After the reaction was completed, it was filtered to obtain a light yellow liquid. The solvent benzene was removed under normal pressure, and ethyl acetoacetate was recovered under reduced pressure to obtain a yellow solid residue.

[0037] The yellow solid residue was placed in the flask without taking it out, and was directly used for the hydrolysis reaction. After the flask was cooled to room temperature, the prepared NaOH dilute alcohol solution (10g NaOH, 60mlH 2 (0, 25ml of absolute ethanol), heated to reflux (80° C.), and hydrolyzed for 2 hours to obtain a dark brown transparent liquid. The liquid in the flask was cooled to 50°C, poured out while hot, and cooled to obtain a solid. Filter, then dissolv...

Embodiment 2～10

[0044] Same as Example 1, reacted under different catalysts and different reaction conditions, the results are shown in Tables 1 to 3.

[0045]

[0046]

[0047]

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Abstract

The invention relates to a preparation method of 3-methyl-normuscone musk (musk ketone), which mainly includes the steps of: (1) obtaining hexadecanedione-(2, 15) by using 1, 10-dibromodecane to react with acetylacetic ether under the existence conditions of inorganic alkali and phase transfer catalyst; (2) under the existence condition of the catalyst, obtaining a target from the hexadecanedione-(2, 15) by 'cyclization' and 'hydrogenation' in turn. The invention is characterized in that the phase transfer catalyst in step (1) is a quaternary alkylammonium salt containing C [12] to C [25]; simultaneously, the reaction of the 1, 10-dibromodecane and the acetylacetic ether is carried out in an aprotic polarity solvent. Compared with the prior art, the musk ketone preparation method proposed by the invention has the advantages of simple process and high yield; the invention is a musk ketone preparation method with more commercial values.

Description

technical field [0001] The present invention relates to a kind of preparation method of 3-methyl cyclopentadecanone (muskone), specifically, it is a kind of 1,10-dibromodecane, ethyl acetoacetate as raw material, through phase transfer catalytic condensation A method for preparing muscone by hydrolysis, cyclization and hydrogenation. Background technique [0002] Muscone (3-methylcyclopentadione) is not only a rare spice, but also a widely used Chinese herbal medicine. Due to the scarcity of natural muskone, the synthesis of muskone has attracted the attention of chemists. [0003] So far, the methods for preparing muskone can be mainly divided into three types: methylation method, cyclic ketone ring expansion method and ring closure method. [0004] (1) Methylation method, that is, the method of inserting a methyl group at the β-position of cyclopentadecanone to obtain 3-methylcyclopentadecone, such as the scientific literature J.Org.Chem., 1971, 36(26): 4124 -4125.; Che...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/385C07C45/72B01J31/02
Inventor 方云进董霞王宁
Owner EAST CHINA UNIV OF SCI & TECH
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