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Method for preparing L-muscone

A technology of musk ketone and compound is applied in the field of preparing L-musk ketone by diastereomer salt-forming separation method, which can solve the problems of unsuitability for industrial production of R-musk ketone, large amount of catalyst, many reaction steps, etc., so as to improve the product quality. The effect of selectivity, less three wastes, and convenient recycling

Active Publication Date: 2020-03-24
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, the main methods for synthesizing R-muskone from 3-methyl-1,15-pentadecanedione are intramolecular asymmetric aldol condensation or dynamic resolution, and these methods generally use a large amount of catalyst. , many reaction steps, low total yield and other shortcomings, not suitable for industrialized production of R-musketone

Method used

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  • Method for preparing L-muscone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] In a 3000mL round bottom flask equipped with a condenser, add 238.4g of racemic muscone, 332.2g of (R)-(-)-mandelic acid methyl ester, 0.24g of p-toluenesulfonic acid and 2000.0mL of tetrahydrofuran. After nitrogen replacement three times , Under the protection of nitrogen, use a laser with a wavelength of 0.7μm, and react at a temperature of 40℃ for 1h. Cool the reaction solution to room temperature and use Na 2 CO 3 Saturated solution (1000.0mL) and saturated NaCl solution (1000.00mL) are washed twice each, anhydrous Na 2 SO 4 After drying, use a rotary evaporator to evaporate the solvent to obtain a liquid crude product containing dextro-musketone that has not participated in the reaction. The content of dextro-musketone is 110.87g as determined by the internal standard.

[0044] The crude product was put into a 500 mL crystallizer, and after crystallization was performed at -5°C, 295.61 g of crude levorotatory enantiomer salt was obtained by filtration, with a yield of ...

Embodiment 2

[0047] In a 3000mL round bottom flask equipped with a condenser, add 238.4g of racemic muscone, 293.04g of (R)-(-)-1-phenylethanol, 2.38g of methanesulfonic acid and 1000.0mL of acetonitrile. After nitrogen replacement for three times , Under the protection of nitrogen, use a laser with a wavelength of 5.2μm to react at a temperature of 60℃ for 2h. Cool the reaction solution to room temperature and use Na 2 CO 3 Saturated solution (1000.0mL) and saturated NaCl solution (1000.00mL) are washed twice each, anhydrous Na 2 SO 4 After drying, use a rotary evaporator to evaporate the solvent to obtain a liquid crude product containing dextro-muskone that has not participated in the reaction. The content of dextro-muskone is 103.23g as determined by the internal standard.

[0048] The crude product was placed in a 500 mL crystallizer, and after crystallization was performed at -10°C, 263.43 g of crude levorotatory enantiomer salt was obtained by filtration, with a yield of 56.70%.

[0049]...

Embodiment 3

[0051] In a 3000mL round-bottomed flask equipped with a condenser, add 238.4g racemic muscone, 498.3g L-(-)-3-phenyllactic acid, 4.77g trifluoromethanesulfonic acid and 1666.67mL ethyl acetate, and replace with nitrogen three times Then, under the protection of nitrogen, a laser with a wavelength of 6 μm was used for reaction at a temperature of 80° C. for 4 hours. Cool the reaction solution to room temperature and use Na 2 CO 3 Saturated solution (1000.0mL) and saturated NaCl solution (1000.00mL) are washed twice each, anhydrous Na 2 SO 4 After drying, use a rotary evaporator to evaporate the solvent to obtain a liquid crude product containing dextro-musketone that has not participated in the reaction. The content of dextro-musketone is 113.10 g determined by internal standard.

[0052] The crude product was placed in a 500 mL crystallizer, and after crystallization was performed at -5°C, 290.44 g of crude levorotatory enantiomer salt was obtained by filtration, with a yield of 5...

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Abstract

The invention discloses a method for preparing L-muscone. The method comprises the following steps: (1) L-muscone in racemic muscone and a chiral hydroxybenzene compound generate L-enantiomer salt under laser irradiation; and (2) crystallization separation and hydrolysis are performed on the L-enantiomer salt to obtain a L-muscone product, wherein the step (1) is carried out in the presence of a Bronsted acid catalyst. Preferably, after hydrolysis in the step (2), separation, purification and other steps are carried out to obtain the L-muscone product. The raw material used in the method is the racemic muscone with a mature production process; batch production can be realized, diastereomer salifying resolution is carried out by adopting laser irradiation, the product selectivity is greatlyimproved, the method is green, pollution-free, and less in production of three wastes, the chiral hydroxybenzene compound is convenient to recover and reusable, the atom economy is high, the productselectivity is high, and the method is suitable for being used in the fields of biology, medical treatment, medicines, spices, cosmetics and the like.

Description

Technical field [0001] The invention belongs to the field of flavors and fragrances and pharmaceutical engineering, and specifically relates to a method for preparing levorotatory muscone by a diastereomeric salt-forming resolution method. Background technique [0002] Muskone, namely 3-methylcyclopentadecanone, is the main source of natural musk's rare fragrance. It can play an excellent role in fixing, accenting and rounding the fragrance, and it is extremely precious in fragrance. At the same time, muscone also has the functions of resuscitating, diminishing filth, dredging collaterals, and dispelling stasis, and can treat stroke, phlegm convulsion, convulsion, nausea, dysphoria, abdominal pain, bruises, carbuncle swelling and poison. Muscone has a chiral center. Natural muscone has a left-handed configuration, while synthetic muscone are basically racemates, that is, an equal mixture of L-muscone and dextro-muscone. Levomuscone is the main active ingredient of natural musk, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/51C07C45/85C07C45/78C07C49/385
CPCC07C45/515C07C67/31C07C45/85C07C45/78C07B2200/07C07C49/385C07C69/73
Inventor 于斌成黄文学张永振
Owner WANHUA CHEM GRP CO LTD
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