CN107602363B - Preparation method of muscone - Google Patents
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- CN107602363B CN107602363B CN201710832770.6A CN201710832770A CN107602363B CN 107602363 B CN107602363 B CN 107602363B CN 201710832770 A CN201710832770 A CN 201710832770A CN 107602363 B CN107602363 B CN 107602363B
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Abstract
The invention relates to a preparation method of muscone, which comprises the following steps: adding 1, 2-diol, 3-methyldienone, toluene and pyridinium p-toluenesulfonate carried by polystyrene resin, stirring, heating, cooling to room temperature, and filtering to obtain a first ketal compound; adding a first solvent and a catalyst, heating and refluxing until the reaction is finished, cooling to room temperature, and filtering to obtain a second ketal compound; adding a first solvent and an acid solution, stirring until the reaction is finished, cooling to room temperature, filtering, washing, separating out a first organic layer, and recovering the solvent in the first organic layer under normal pressure to obtain a first ketene compound; adding an alcohol solution and a metal catalyst into a reaction bottle, repeatedly replacing gas in the reaction bottle by using nitrogen and hydrogen, filtering and performing reduced pressure rectification after the reaction is finished at normal temperature and normal pressure to obtain the muscone. The preparation method of muscone provided by the invention has the advantages of simple process flow and low cost, and can be used for industrial mass production.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, and particularly relates to a preparation method of muscone.
Background
Muscone (3-methylcyclopentadecanone) is an important perfume, mainly found in natural musk. The natural Moschus is dry secretion of Moschus forest Musk, Moschus equi or Moschus of original Moschus of Cervidae, and has rare source, so the natural muscone in Moschus is more rare. Therefore, chemists have been working on finding efficient, low cost methods of preparation.
At present, the synthesis method of muscone mainly comprises a cyclic ketone ring expanding method and a ring closing method. Specifically, (1) cyclic ketone ring expansion method: cyclododecanone was the most expensive and readily available by-product of the petroleum industry and was first used as a feedstock for the ring expansion process in the Firmenich laboratory. Through the development of decades, the ring expanding method simplifies and shortens the synthetic route, but the synthetic route is still longer, so the content of the musk ketone in the product is lower; (2) a closed-loop method: the closed-loop method is to obtain a target cyclic compound from a chain compound through end-to-end connection, and comprises a plurality of intermediate closed-loop methods, and specifically comprises an aldol condensation closed-loop method, an alcohol ketone condensation closed-loop method, a Dieckmann ester condensation closed-loop method, an intramolecular acylation closed-loop method, a free radical addition closed-loop method, a Prins reaction closed-loop method, a Wittig-Emmons-Horner reaction closed-loop method, an intramolecular 1, 3-dipolar addition closed-loop method, an intramolecular nucleophilic substitution closed-loop method, a terminal alkyne oxidation coupling closed-loop method and the like.
However, the existing method for preparing the muscone has complex flow, high cost and complicated preparation process, and limits the industrial mass production of the muscone.
Disclosure of Invention
Based on the above, the invention aims to provide a preparation method of muscone with simple process and low cost so as to meet the requirement of practical application.
The invention provides a preparation method of muscone, which comprises the following steps:
adding 1, 2-diol loaded with polystyrene resin with a first preset mass, 3-methyldienone with a second preset mass, toluene with a first preset volume and a first catalyst with a third preset mass into a first reaction kettle, stirring and heating for a first preset time, cooling to room temperature, and filtering to obtain a first ketal compound loaded with polystyrene resin;
adding the first ketal compound loaded by the polystyrene resin, a first solvent with a second preset volume and a second catalyst with a fourth preset mass into a second reaction kettle, heating and refluxing until the reaction is finished, cooling to room temperature, and filtering to obtain a second ketal compound loaded by the polystyrene resin;
adding the second ketal compound loaded by polystyrene resin, the first solvent with a second preset volume and the acid solution with a third preset volume into a third reaction kettle, stirring at a first preset temperature until the reaction is finished, cooling to room temperature, filtering, washing, separating out a first organic layer, and recovering the solvent in the first organic layer under normal pressure to obtain a first ketene compound;
adding the first ketene compound, an alcoholic solution with a fourth preset volume and a metal catalyst with a fifth preset mass into a reaction bottle, repeatedly replacing air in the reaction bottle with nitrogen for a first preset number of times, then repeatedly replacing the nitrogen in the reaction bottle with hydrogen for a second preset number of times, filtering under normal temperature and normal pressure until the reaction is finished, and performing reduced pressure rectification to obtain the muscone.
The preparation method of muscone provided by the invention comprises the steps of firstly preparing a first ketal compound in a reaction kettle, preparing a second ketal compound according to the first ketal compound, then preparing a first ketene compound according to the prepared second ketal compound, and finally preparing the muscone. The preparation method of muscone provided by the invention is simple in process and low in cost, can be applied to industrial production, and meets the requirements of practical application.
The method for producing muscone is characterized in that the first ketal compound is 2, 6-dimethyl-octadeca-2, 17-diene-8-ketal, the second ketal compound is 3-methylcyclopentadec-6-enone, and the first enone compound is 3-methylcyclopentadec-6-enone.
The preparation method of the muscone is characterized in that the first ketal compound is 9-methylheptadec-1, 16-diene-7-ketal, the second ketal compound is 3-methylcyclopentadec-9-ene ketal, and the first ketene compound is 3-methylcyclopentadec-9-ketene.
The preparation method of the muscone comprises the following steps of setting the first preset mass to be 2kg, setting the second preset mass to be 1.28kg, setting the first preset volume to be 20L, setting the third preset mass to be 7.3g, and setting the first preset time to be 10 h.
The preparation method of the muscone comprises the following steps of setting the first preset mass to be 2kg, setting the second preset mass to be 1.38kg, setting the first preset volume to be 20L, setting the third preset mass to be 4.4g, and setting the first preset time to be 15 h.
The preparation method of the muscone comprises the steps of taking dichloromethane as the first solvent, taking the second preset volume as 20L, taking the fourth preset mass as 1.3g, and taking Grubbs second generation catalyst as the second catalyst.
The preparation method of the muscone comprises the steps of taking tetrahydrofuran as the first solvent, taking the second preset volume as 20L, taking the fourth preset mass as 2.86g, and taking Grubbs as the second catalyst.
The preparation method of the muscone, wherein the first ketene compound is 3-methyl cyclopentadecano-6-ketene, the acid solution is hydrochloric acid, the second preset volume is 20L,
the first solvent is dichloromethane, the third preset volume is 1L, and the first preset temperature is 40 ℃.
The preparation method of the muscone comprises the steps of preparing a first ketene compound from 3-methylcyclopentadecan-9-ketene, preparing an acid solution from formic acid, preparing a second preset volume of 20L, preparing a first solvent from tetrahydrofuran, preparing a third preset volume of 1L, and preparing a first preset temperature of 40 ℃.
The preparation method of the muscone comprises the steps of preparing an alcoholic solution, wherein the alcoholic solution is methanol or ethanol, the metal catalyst is palladium carbon or metal nickel, the fourth preset volume is 1L or 2L, the fifth preset mass is 3.5g or 40g, the first preset times are 5, and the second preset times are 3.
Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention.
Drawings
Fig. 1 is a flow chart of a method for preparing muscone according to an embodiment of the present invention.
Detailed Description
To facilitate an understanding of the invention, the invention will now be described more fully with reference to the accompanying drawings. Preferred embodiments of the present invention are shown in the drawings. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
Example one
Referring to fig. 1, a method for preparing muscone includes the following steps:
(1) preparation of polystyrene resin-loaded first ketal compound:
adding 2kg of polystyrene resin-loaded 1, 2-diol (I), second preset mass (1.28kg or 1.38kg) of 3-methyldienone (II), 20L of toluene and third preset mass (4.4g or 7.3g) of first catalyst into a 50L glass reaction kettle equipped with a thermometer, a mechanical stirrer and a water separator, stirring and heating to 40-140 ℃, reacting for a first preset time (2-20 h), cooling to room temperature, and filtering to obtain a polystyrene resin-loaded first ketal compound, wherein the first ketal compound is 2, 6-dimethyl-octadeca-2, 17-diene-8-ketal or 9-methylheptadec-1, 16-diene-7-ketal.
Wherein the polystyrene resin-supported 1, 2-diol (k is an integer of 4 to 18) has the structural characteristics of:
the chain length of the 1, 2-diol connected with the polystyrene is k +3, k is an integer from 4 to 18, and the degree of substitution is 0.4-1.2 mol/kg.
The structural characteristics of the 3-methyl dienone are as follows:
wherein the total length of the carbon chain is (m +2) + (n +2) +3 equal to 17, m and n are integers more than 1, and the sum of m and n is 10. R bound by two double bonds1、R2、R3、R4All of the groups may be methyl groups or hydrogen atoms, and some of the groups may be methyl groups or hydrogen atoms.
Further, the first catalyst may be toluene sulfonic acid, concentrated hydrochloric acid, pyridinium p-toluene sulfonate, methane sulfonic acid, or trifluoromethane sulfonic acid. In this example, the first catalyst was pyridinium p-toluenesulfonate. The molar ratio of the 3-methyl dienone (II), the polystyrene resin supported 1, 2-diol (I) and the first catalyst is 1.0-10.0: 1.0: 0.01-0.05. It is also to be noted here that the above solvent may be xylene, cyclohexane, n-hexane, n-pentane, n-heptane, dichloromethane or 1, 2-dichloroethane in addition to toluene.
(2) Preparation of polystyrene resin-loaded second ketal compound:
adding the first ketal compound carried by polystyrene resin, 20L of first solvent (comprising dichloromethane or tetrahydrofuran) and a fourth catalyst (comprising Grubbs second generation catalyst or Grubbs first generation catalyst) with a preset mass (1.3g or 2.86g) into a 50L glass reaction kettle equipped with a thermometer, a mechanical stirrer and a water separator, heating (20-100 ℃) to reflux to react for 2-20 h, cooling to room temperature, and filtering to obtain the second ketal compound carried by polystyrene resin (the second ketal compound is 3-methylcyclopentadec-6-ene ketal or 3-methylcyclopentadec-9-ene ketal).
In addition, the second catalyst can be Grubbs-Hoveyda second generation catalyst, and the molar ratio of the second catalyst to the first ketal compound is 0.0005-0.01: 1.0.
(3) Preparation of the first enone compound:
adding the second ketal compound carried by polystyrene resin, 20L of a first solvent (comprising dichloromethane or tetrahydrofuran) and a third preset volume of acid solution into a 50L glass reaction kettle provided with a thermometer, a mechanical stirrer and a water separator, stirring at 0-80 ℃ until the reaction is finished for 2-15 h, cooling to room temperature, filtering, washing, separating out a first organic layer, and recovering the solvent in the first organic layer under normal pressure to obtain a first ketene compound (the first ketene compound is 3-methyl pentadecac-6-ketene or 3-methyl pentadecac-9-ketene).
It is to be added here that the acid solution can be hydrochloric acid, hydrobromic acid, trifluoroacetic acid, formic acid, dilute sulfuric acid, potassium hydrogen sulfate or sodium hydrogen sulfate. Wherein the molar ratio of the acid solution to the second ketal compound is 0.05-0.2: 1.0. The first solvent is dichloromethane, 1, 2-dichloroethane, tetrahydrofuran, 2-methyltetrahydrofuran or cyclopentyl methyl ether.
(4) Preparation of muscone:
adding the first ketene compound, a fourth alcohol solution (methanol, ethanol, isopropanol or n-propanol) with a preset volume (1L or 2L) and a fifth metal catalyst (palladium carbon or metal nickel) with a preset mass (3.5g or 40g) into a reaction bottle, repeatedly replacing air in the reaction bottle with nitrogen for 5 times, then repeatedly replacing the nitrogen in the reaction bottle with hydrogen (1-20 atm) for 3 times, reacting at 0-60 ℃ for 2-15 h, filtering, and performing reduced pressure distillation to obtain the muscone.
The preparation method of muscone provided by the invention comprises the steps of firstly preparing a first ketal compound in a reaction kettle, preparing a second ketal compound according to the first ketal compound, then preparing a first ketene compound according to the prepared second ketal compound, and finally preparing the muscone. The preparation method of muscone provided by the invention is simple in process and low in cost, can be applied to industrial production, and meets the requirements of practical application.
Example two
(1) Preparation of polystyrene resin-supported 2, 6-dimethyl-octadeca-2, 17-diene-8-ketal (shown below, k ═ 9):
2kg of polystyrene resin-supported 1, 2-diol having a degree of substitution of 0.73mol/kg, 1.28kg of 2, 6-dimethyl-octadeca-2, 17-dien-8-one, 20L of toluene and 7.3g of pyridinium p-toluenesulfonate were charged into a 50L glass reactor equipped with a thermometer, mechanical stirring and a water separator. Heating, refluxing and water dividing for 10h under the stirring condition. After cooling to room temperature, the mixture was filtered, and the filtrate obtained by the filtration was used for the next reaction, and the polystyrene resin was washed with dichloromethane 3 times (10 liters each) and used for the next step.
(2) Preparation of polystyrene resin-loaded 3-methylcyclopentadec-6-eneketal:
A50L glass reactor equipped with a thermometer, mechanical stirring and reflux condenser was charged with the polystyrene resin-supported 2, 6-dimethyl-octadeca-2, 17-diene-8-ketal obtained in the previous step, 20L of methylene chloride and 1.3g of Grubbs second generation catalyst. Heating and refluxing until the reaction is finished (the reaction end point can be judged by using the reaction system with or without gas overflow). After cooling to room temperature, the mixture was filtered, and the filtrate obtained by the filtration was used for the next reaction, and the polystyrene resin was washed with fresh dichloromethane 3 times (10 liters each) and used for the next step.
(3) Preparation of 3-methylcyclopentadecan-6-enone:
3-methylcyclopentadec-6-eneketal carried by the polystyrene resin obtained in the previous step, 20L of dichloromethane and 1L of 6N hydrochloric acid were added to a 50L glass reaction kettle equipped with a thermometer, a mechanical stirring tube and a reflux condenser tube, and the reaction was stirred at 40 ℃ until completion. After cooling to room temperature, filtration was carried out, the polystyrene resin was washed with water 2 times (10 liters each time), with fresh dichloromethane 2 times (10 liters each time), the filtrate and the washing solution were combined, the organic layer was separated, the solvent was recovered at normal pressure to obtain 350g of crude 3-methylcyclopentadecene for further use.
(4) Preparation of 3-methylcyclopentadecanone (muscone):
adding a 3-methylcyclopentadecene crude product, 1L methanol and 3.5g of palladium-carbon with the mass fraction of 10% into a 2L three-mouth round-bottom bottle, replacing the air in the kettle with nitrogen for 5 times, then replacing the nitrogen in the kettle with hydrogen for 3 times, and reacting at room temperature and normal pressure until the reaction is finished. The catalyst is recovered after filtration, the solvent methanol is recovered from the filtrate under normal pressure, and the pure product of 321.3g of 3-methyl cyclopentadecanone (muscone) is obtained by vacuum rectification, and the corresponding yield is 92.3 percent.
EXAMPLE III
(1) Resin preparation of polystyrene resin-supported 9-methylheptadec-1, 16-diene-7-ketal (shown below, k ═ 13):
2kg of polystyrene resin-supported 1, 2-diol having a degree of substitution of 0.87mol/kg, 1.38kg of 9-methylheptadec-1, 16-dien-7-one, 20L of toluene and 4.4g of pyridinium p-toluenesulfonate were charged in a 50L glass reactor equipped with a thermometer, mechanical stirring and a water separator, and heated under reflux for 15 hours. After cooling to room temperature, the mixture was filtered, and the filtrate obtained by the filtration was used for the next reaction, and the polystyrene resin was washed with dichloromethane 3 times (10 liters each time) and used for the next step.
(2) Preparation of polystyrene resin-loaded 3-methylcyclopentadec-9-eneketal:
A50L glass reactor equipped with a thermometer, mechanical stirring and reflux condenser was charged with 9-methylheptadec-1, 16-diene-7-ketal supported on the polystyrene resin obtained in the previous step, 20L tetrahydrofuran and 2.86g of Grubbs first generation catalyst. Heating and refluxing until the reaction is finished (the reaction end point can be judged by using the reaction system with or without gas overflow). After cooling to room temperature, the mixture was filtered, the filtrate obtained by the filtration was used for the next reaction, and the polystyrene resin was washed with fresh tetrahydrofuran 3 times (10 liters each time) and used for the next step.
(3) Preparation of 3-methylcyclopentadecan-9-enone:
3-methylcyclopentadec-9-eneketal loaded on polystyrene resin obtained in the previous step, 20L tetrahydrofuran and 1L 85% formic acid solution were added to a 50L glass reaction kettle equipped with a thermometer, a mechanical stirring and reflux condenser, and stirred at 40 ℃ until the reaction was completed. Cooling to room temperature, filtering, washing the polystyrene resin with water for 2 times (10L each time) and fresh tetrahydrofuran for 2 times (10L each time), combining the filtrate and washing liquid, separating out an organic layer, recovering the solvent at normal pressure to obtain 430g of crude 3-methylcyclopentadec-9-enone for further use.
(4) Preparation of 3-methylcyclopentadecanone (muscone)
Adding 3-methyl cyclopentadecanone-9-ketene crude product, 2L ethanol and 40 skeleton nickel into a 5L stainless steel hydrogenation kettle, replacing the air in the kettle with nitrogen for 5 times, then replacing the nitrogen in the kettle with hydrogen for 3 times, and reacting for 10 hours at 60 ℃ under 6 atmospheres. Cooling to room temperature, filtering, recovering catalyst, recovering solvent ethanol from the filtrate at normal pressure, and vacuum rectifying to obtain 392g of pure 3-methylcyclopentadecanone (muscone) with corresponding yield of 95.3%.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (9)
1. The preparation method of muscone is characterized by comprising the following steps:
adding 1, 2-diol loaded with polystyrene resin with a first preset mass, 3-methyldienone with a second preset mass, toluene with a first preset volume and a first catalyst with a third preset mass into a first reaction kettle, stirring and heating for a first preset time, cooling to room temperature, and filtering to obtain a first ketal compound loaded with polystyrene resin, wherein the first ketal compound is 9-methylheptadecyl-1, 16-diene-7-ketal;
adding the first ketal compound loaded by the polystyrene resin, a first solvent with a second preset volume and a second catalyst with a fourth preset mass into a second reaction kettle, heating and refluxing until the reaction is finished, cooling to room temperature, and filtering to obtain a second ketal compound loaded by the polystyrene resin, wherein the second ketal compound is 3-methylcyclopentadec-9-eneketal;
adding the second ketal compound loaded by polystyrene resin, the first solvent with a second preset volume and the acid solution with a third preset volume into a third reaction kettle, stirring at a first preset temperature until the reaction is finished, cooling to room temperature, filtering, washing, separating out a first organic layer, and recovering the solvent in the first organic layer under normal pressure to obtain a first ketene compound, wherein the first ketene compound is 3-methyl cyclopentadec-9-ketene;
adding the first ketene compound, an alcoholic solution with a fourth preset volume and a metal catalyst with a fifth preset mass into a reaction bottle, repeatedly replacing air in the reaction bottle with nitrogen for a first preset number of times, then repeatedly replacing the nitrogen in the reaction bottle with hydrogen for a second preset number of times, filtering and performing reduced pressure rectification after the reaction is finished at normal temperature and normal pressure to obtain the muscone;
the first solvent is dichloromethane or tetrahydrofuran, the first catalyst comprises toluene sulfonic acid, concentrated hydrochloric acid, pyridinium p-toluene sulfonate, methane sulfonic acid or trifluoromethane sulfonic acid, the second catalyst comprises a Grubbs second generation catalyst or a Grubbs first generation catalyst, and the metal catalyst comprises palladium on carbon or metallic nickel.
2. The method of producing muscone according to claim 1, wherein the first ketal compound is 2, 6-dimethyl-octadeca-2, 17-dien-8-ketal, the second ketal compound is 3-methylcyclopentadec-6-enone, and the first enone compound is 3-methylcyclopentadec-6-enone.
3. The method for preparing muscone according to claim 2, characterized in that the first preset mass is 2kg, the second preset mass is 1.28kg, the first preset volume is 20L, the third preset mass is 7.3g, and the first preset time is 10 h.
4. The method for preparing muscone according to claim 1, wherein the first preset mass is 2kg, the second preset mass is 1.38kg, the first preset volume is 20L, the third preset mass is 4.4g, and the first preset time is 15 h.
5. The method of producing muscone according to claim 3, wherein the first solvent is dichloromethane, the second predetermined volume is 20L, the fourth predetermined mass is 1.3g, and the second catalyst is Grubbs second generation catalyst.
6. The method of producing muscone according to claim 4, wherein the first solvent is tetrahydrofuran, the second predetermined volume is 20L, the fourth predetermined mass is 2.86g, and the catalyst is Grubbs first generation catalyst.
7. The method of producing muscone according to claim 5, wherein the first enone compound is 3-methylcyclopentadecan-6-enone, the acid solution is hydrochloric acid, the second predetermined volume is 20L, the first solvent is dichloromethane, the third predetermined volume is 1L, and the first predetermined temperature is 40 ℃.
8. The method of claim 6, wherein the first ketene compound is 3-methylcyclopentadecan-9-ketene, the acid solution is formic acid, the second predetermined volume is 20L, the first solvent is tetrahydrofuran, the third predetermined volume is 1L, and the first predetermined temperature is 40 ℃.
9. The method for preparing muscone according to claim 1, wherein the alcohol solution is methanol or ethanol, the metal catalyst is palladium on carbon or metal nickel, the fourth predetermined volume is 1000ml or 2000ml, the fifth predetermined mass is 3.5g or 40g, the first predetermined number of times is 5, and the second predetermined number of times is 3.
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