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Preparation method of trimethyl macrocyclic ketone

A technology of methylcyclopentadecone and macrocyclic ketone, which is applied in the field of preparation of muskone, 3-methylcyclotetradecone and trimethylmacroketone, can solve the problem of long storage time, complex operation, reaction Long cycle and other problems, to achieve the effect of increased yield and faster reaction speed

Inactive Publication Date: 2011-02-23
刘畅
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of the synthetic route reported in Tetrahedron, 2002, 58: 8269-8290 as Huellmann Michael et al. is 67%, but there are still problems such as long reaction cycle, complicated operation and inconvenient post-processing
It has been found that 3-methylcyclotetradecone and muskone (3-methylcyclopentadecone) are exactly the same in terms of fragrance and biological activity, and it is more It is stable, easy to synthesize, and has a long storage time. After searching, no reports of synthesis or listing were found.

Method used

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  • Preparation method of trimethyl macrocyclic ketone
  • Preparation method of trimethyl macrocyclic ketone
  • Preparation method of trimethyl macrocyclic ketone

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Embodiment 1

[0030] Add 100 mL of dry tetrahydrofuran, 20 g of ethyl acetoacetate, 2.21 g of Na, and 35 mL of triethylamine into a 250 mL flask, stir at room temperature for 20 min, and add 11 g (36.7 mmol) of a tetrahydrofuran solution of 1,10-dibromodecane dropwise 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,

[0031] Recrystallized ...

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Abstract

The invention discloses a preparation method of 3-methyl macrocyclic ketone, which belongs to the food additive field. The preparation method comprises the following steps of: performing homogeneous reaction on ethyl acetoacetate and 1,10-dibromodecane or 1,9-dibromononane under the catalytic condition of organic alkali so as to generate 2,15-hexadecanedione or 2,14-pentadecane diketone; in the room temperature and the normal pressure, in Ti-medium Ti Cl4-organic amine system, adding dehydrated silica gel in the 2,15-hexadecanedione or 2,14-pentadecane diketone and performing a ring-closing reaction and a hydrogenated reduction reaction so as to prepare 3-methylcyclopentadecanone or 3-methyl cyclotetradecanone. The preparation method has the advantages that: the method has the characteristics of industrialized production and the like, is a preparation method of the muskone and the 3-methyl cyclotetradecanone with commercial value, has a short reaction period and is convenient to operate; and post-treatment can be conveniently performed.

Description

technical field [0001] The invention belongs to a method for preparing trimethylmacroketone, in particular to a method for synthesizing muskone (3-methylcyclopentadecone) and 3-methylcyclotetradecone, and belongs to the field of food additives. 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 se...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/69B01J31/02C07C49/385A23L27/20
CPCA23L27/20C07C45/61C07C45/68C07C2601/18C07C49/385C07C49/12
Inventor 高旌朱守一栗进才陈旺兴刘畅
Owner 刘畅