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Process for preparing musk ketone

A preparation process, the technology of muscone, applied in the field of biomedicine, can solve the problems of complex operation, inconvenient post-processing, long reaction cycle, etc., and achieve the effect of accelerating the reaction speed and improving the yield

Inactive Publication Date: 2014-09-10
高旌
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the yield of the synthetic route reported in Tetrahedron, 2002, 58:8269-8290 by Huellm ann Michael et al. is 67%, but there are still problems such as long reaction cycle, complicated operation, and inconvenient post-processing

Method used

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  • Process for preparing musk ketone
  • Process for preparing musk ketone
  • Process for preparing musk ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add 100 mL of dry tetrahydrofuran, 20 g of ethyl acetoacetate, 2.21 g of NaH, and 35 mL of triethylamine into a 250 mL flask, stir at room temperature for 20 min, and add dropwise 11 g (36.7 mmol) of 1,10-dibromodecane in tetrahydrofuran under stirring . After the reaction was completed, a light yellow liquid was obtained by filtration, and the solvent was recovered under reduced pressure to obtain a yellow solid residue. After the flask was cooled to room temperature, the prepared aqueous alkali solution (10g NaOH, 70mL water, 30mL absolute ethanol) was added thereto, heated to reflux at 85°C for 2 hours, the brown liquid was collected by filtration while it was hot, and it was left to cool to obtain a solid. Filter, then dissolve the solid with about 200 mL of dichloromethane, and remove the insoluble matter by filtration to obtain a light yellow liquid. The organic phase was recovered under reduced pressure to obtain a gray solid, which was recrystallized with v (et...

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Abstract

The invention relates to a process for preparing musk ketone, which comprises the following steps of: adopting catalyzing ethyl acetoacetate and 1,10-dibromodecane as raw materials to generate 2,15-hexadecanedione through sodium hydride (calcium hydride or a mixture formed by sodium hydride and calcium hydride) and organic base under the homogeneous condition; and then adding dehydrated silica gel to perform a closed loop and hydrogenation reduction reaction so as to prepare 3-methyl cyclopentadecanone. The reaction time is short (2 to 4 hours). The yield is greatly improved (by over 90 percent). The technology has mild reaction, high yield and few three wastes and is suitable for industrial production.

Description

technical field [0001] The invention belongs to an improved process route for synthesizing muskone (3-methylcyclopentadecanone). Specifically, it belongs to the field of biomedicine, a chemical total synthesis of natural active ingredients. Background technique [0002] Muscone is the main component of musk, a famous traditional Chinese medicine, and an important base phase component of high-grade fragrances. Due to the scarcity of wild musk deer and the needs of society, the current market is in short supply. In recent years, people have made research efforts and developed many synthetic methods. So far, the methods for preparing muskone are mainly divided into three types: methylation method, cyclic ketone ring expansion method and ring closure method. Among them, the current research focuses on the closed-loop method, such as the 2,15-hexadecanedione produced by the reaction of ethyl acetoacetate and 1,10-dibromodecane, which is then condensed and hydrogenated. A serie...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/385C07C45/65
Inventor 李琦王松婷牛海军李翔宇高旌俞年军刘亚华
Owner 高旌
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