CN107698450B - Synthetic method of irisone spice - Google Patents
Synthetic method of irisone spice Download PDFInfo
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- CN107698450B CN107698450B CN201710966824.8A CN201710966824A CN107698450B CN 107698450 B CN107698450 B CN 107698450B CN 201710966824 A CN201710966824 A CN 201710966824A CN 107698450 B CN107698450 B CN 107698450B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
- C07C29/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings in a non-condensed rings substituted with hydroxy groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
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Abstract
The invention discloses a synthetic method of iridate perfume, which relates to the technical field of fine chemical engineering, and is characterized in that phenol and tert-butyl alcohol are used as initial raw materials for alkylation reaction, and then are hydrogenated and then are subjected to acetylation reaction with acetic anhydride to produce iridate, so that the raw materials are easy to obtain and the yield is high; petroleum ether is used as an organic solvent for alkylation reaction and hydrogenation reaction, so that the defects of incomplete reaction and inactivation after the catalyst is mechanically used in the hydrogenation process are overcome, and the distillation process step when dichloroethane is used as the solvent in the common alkylation reaction can be omitted; and the petroleum ether has low boiling point and is easy to recycle, thereby avoiding the environmental pollution caused by the discharge of the organic solvent into the wastewater and simultaneously reducing the production cost.
Description
The technical field is as follows:
the invention relates to the technical field of fine chemical engineering, and in particular relates to a synthetic method of an iridate spice.
Background art:
irises are chemically known as p-tert-butylcyclohexyl acetate and are not found in nature. Molecular formula C12H22O2CAS number: 32210-23-4, colorless transparent oily liquid, sweet and fruity, and rich fragrance of radix aucklandiae and flos Chrysanthemi, and can be used in various essences, especially in soap and washing powder essence. Relative Density of Iridonate (25 ℃): 0.9350 to 0.9400, refractive index (20 ℃): 1.4500-1.4540, boiling point 246 deg.C (105-106 deg.C/1.2 kPa), and is soluble in organic solvent such as ethanol and ethylene glycol, and insoluble in water. Iris ester is mixture of cis-isomer and trans-isomer, the ratio of cis-isomer and trans-isomer is about 3:7, the fragrance of cis-isomer is stronger than that of trans-isomer, and high cis-form iridate ester can be widely appliedFor use in a variety of fragrance formulations, particularly in floral and mixed floral fragrances, the use of a base fragrance of the fatty note type is preferred.
Irimate has sweet cream fragrance, pinus aucklandia, floral fragrance and green plant fragrance, is a common synthetic perfume, is very useful in the whole modern perfume, and can be used for injecting warm characteristics into the floral essence. The fragrance type deodorant is widely applied to daily chemical essence formulas such as perfume essence, cosmetic essence, soap essence and the like, the dosage is within 20%, IFRA is not limited to be specified, the fragrance type deodorant can be stably used in most essence products, and the fragrance type deodorant can be well fused with fragrance of linalyl acetate, terpinyl acetate and iononyl acetate, and comprises perfume, cream, antiperspirant, deodorant, shampoo, perfumed soap, cleaning powder and the like, and is particularly useful for perfumed soap, cologne, shampoo, skin cream and face cream.
Iris ester is one of the important synthetic perfumes with wider application, the demand of recent years is gradually expanded, the general synthetic method takes phenol as the initial raw material, sulphuric acid as the catalyst, isobutene gas is introduced for alkylation to form p-tert-butyl phenol, then catalytic hydrogenation is carried out to form p-tert-butyl cyclohexanol, and finally the iri ester is obtained by esterification with acetic acid.
The invention content is as follows:
the technical problem to be solved by the invention is to provide a synthetic method of irimate spice, which has the advantages of easily obtained raw materials, high product yield, high final product content of more than 98.5 percent and 30 percent of cis-isomer content in the product, so that the final product has pure and soft fragrance to meet the fragrance regulation requirements of essence spice.
The technical problem to be solved by the invention is realized by adopting the following technical scheme:
a method for synthesizing iritate spice comprises the following steps:
a) firstly, adding petroleum ether into a three-mouth glass flask by weighing and metering, then adding anhydrous aluminum trichloride into the glass flask, starting a stirrer and a heat and cold exchange all-in-one machine, reducing the temperature of the glass flask to 10-15 ℃, slowly adding phenol into the glass flask, and continuing stirring for 0.5h after the feeding is finished;
b) continuously maintaining the temperature of the glass flask at 10-15 ℃, dropwise adding tert-butyl alcohol into the glass flask by using a dropwise adding pump, controlling the dropwise adding time to be 2 hours, raising the temperature of the kettle to 120-140 ℃ after dropwise adding, and continuously stirring for 2-4 hours; sampling and carrying out chromatographic detection, when the content of phenol is less than or equal to 0.5%, reducing the temperature of a reaction system to 15 ℃, starting a stirrer and a heat and cold exchange all-in-one machine, slowly adding clear water for extraction and quenching, stopping the reaction, and controlling the temperature of a reaction kettle to be less than 40 ℃ in the extraction and quenching process;
c) transferring the generated p-tert-butylphenol reaction liquid to a separating funnel, standing and layering for 0.5h, putting an oil layer into a beaker, adding petroleum ether into a water layer, stirring for 0.5h, standing and layering, merging the oil layers, putting into the beaker, and concentrating the water layer to a waste liquid collecting barrel; adding 5% sodium hydroxide solution into a beaker of the oil layer, starting a stirrer to perform alkaline washing on the collected oil layer, stirring for 0.5h, standing and layering for 0.5h, and concentrating the alkaline solution layer into a waste liquid collecting barrel; adding clear water into the oil layer for washing, stirring for 0.5h, standing for layering for 0.5h, transferring the oil layer into a hydrogenation reaction kettle, and collecting the water layer into a waste liquid collecting barrel;
d) adding a 5% palladium-carbon catalyst into a hydrogenation reaction kettle in a fixed amount, sealing the hydrogenation reaction kettle, replacing the hydrogenation reaction kettle with nitrogen for 4-6 times, then filling the nitrogen to the pressure of 2.0Mpa, replacing the hydrogenation reaction kettle with hydrogen for 4-6 times after the system pressure is stable, then filling the hydrogen, and adjusting the pressure of the hydrogenation reaction kettle to 2.0 Mpa; closing a hydrogen inlet valve after the system pressure is stable, heating to 80-150 ℃, opening the hydrogen valve after the reaction system pressure is balanced, and keeping the reaction pressure at 2.0Mpa for 5-10 h;
e) sampling every 2h after 5h of reaction for chromatographic detection, ending the reaction when the content of the p-tert-butylphenol is less than or equal to 0.5 percent, and releasing pressure; filtering the generated reaction liquid of the tert-butyl cyclohexanol, transferring liquid phase filtrate into a rotary evaporator, cleaning a solid phase catalyst with petroleum ether, transferring the cleaned solid phase catalyst into a hydrogenation reaction kettle, and carrying out the next batch of hydrogenation reaction;
f) starting the rotary evaporator in the step e) to heat, recovering petroleum ether at normal pressure and at the kettle temperature of 60-90 ℃, concentrating and recycling the collected petroleum ether, and transferring the bottom liquid of the bottle to a four-neck flask;
g) adding acetic anhydride and p-toluenesulfonic acid into a four-neck flask in a metering manner, starting a stirrer, starting a heat and heat exchange all-in-one machine for heating, controlling the reaction temperature to be 100-120 ℃, reacting for 3-5 h, transferring the reaction liquid into a rotary evaporator, recovering acetic acid at normal pressure, and transferring the bottom liquid of the flask into a beaker;
h) adding 5% sodium hydroxide solution into a beaker in a metered manner, starting a stirrer to carry out alkali washing on the collected bottom liquid of the bottle, stirring for 0.5h, standing and layering for 0.5h, concentrating an alkali liquid layer into a waste liquid collecting barrel, adding clear water into an oil layer to wash, stirring for 0.5h, standing and layering for 0.5h, concentrating a water layer into the waste liquid collecting barrel, transferring the oil layer into a rotary evaporator, starting the rotary evaporator to heat, and starting a vacuum pump to collect the irimate.
The mass ratio of the petroleum ether to the phenol in the step a) is 1.0: 1-5.0: 1, preferably 2.0: 1-3.0: 1. The molar ratio of the aluminum trichloride to the phenol is 0.5:1 to 5.0:1, preferably 0.5:1 to 1.0: 1.
The molar ratio of the tert-butyl alcohol to the phenol in the step b) is 1.0: 1-5.0: 1, preferably 1.0: 1-1.5: 1.
The mass ratio of the petroleum ether to the water layer in the step c) is 0.5: 1-2: 1, preferably 0.5: 1-1: 1; the mass ratio of the sodium hydroxide solution to the reaction liquid oil layer is 0.2: 1-2: 1, preferably 0.2: 1-1: 1; the mass ratio of the clear water to the reaction liquid oil layer is 0.5: 1-2: 1, and preferably 0.5: 1-1: 1.
The material of the hydrogenation reaction kettle in the step d) is stainless steel, and the design pressure is 0-5 MPa.
The molar ratio of acetic anhydride to p-tert-butylcyclohexanol in the step g) is 1.0: 1-5.0: 1, preferably 1.5: 1-2.0: 1; the dosage of the p-toluenesulfonic acid is 0.5-5 wt%, preferably 1.0-2.0 wt% of the total dosage.
The mass ratio of the 5% sodium hydroxide solution to the bottle base solution in the step h) is 0.2: 1-2: 1, preferably 0.2: 1-1: 1; the mass ratio of the clean water to the oil layer is 0.5: 1-2: 1, and preferably 0.5: 1-1: 1.
The invention has the beneficial effects that:
1) phenol and tert-butyl alcohol are used as initial raw materials for alkylation reaction, and then are hydrogenated to be subjected to acetylation reaction with acetic anhydride to produce irigenin, so that the raw materials are easy to obtain, the yield is high, the method is suitable for small-scale preparation of irigenin in a laboratory, and the process repeatability is good;
2) petroleum ether is used as an organic solvent for alkylation reaction and hydrogenation reaction, so that the defects of incomplete reaction and inactivation after the catalyst is mechanically used in the hydrogenation process are overcome, and the distillation process step when dichloroethane is used as the solvent in the common alkylation reaction can be omitted; the petroleum ether has low boiling point and is easy to recycle, thereby avoiding the environmental pollution caused by the discharge of the organic solvent into the wastewater and simultaneously reducing the production cost;
3) the acetylation reaction of the tert-butyl cyclohexanol and acetic anhydride can generate a byproduct acetic acid, and the acetic acid is recycled; the current general process for producing irigenin by esterification reaction of p-tert-butyl cyclohexanol and acetic acid can generate a large amount of acetic acid wastewater, so that the post-treatment cost of the wastewater is greatly increased;
4) the content of the finished product irisone reaches more than 98.5%, and the content of cis-isomer in the product reaches 30%, so that the product has pure and soft fragrance and meets the requirements of flavor and fragrance blending.
The specific implementation mode is as follows:
in order to make the technical means, the creation characteristics, the achievement purposes and the effects of the invention easy to understand, the invention is further described with the specific embodiments.
Examples
a) 190g of petroleum ether is added into a three-neck glass flask, 68g of anhydrous aluminum trichloride is added into the glass flask, a stirrer and a heat and cold exchange all-in-one machine are started, and the temperature of the glass flask is reduced to 15 ℃.94 g of phenol were slowly added to the glass flask and stirring was continued for 0.5h after the end of the charge.
b) And continuously maintaining the temperature of the glass flask at 15 ℃, dropwise adding 90g of tert-butyl alcohol into the glass flask by using a dropwise adding pump, controlling the dropwise adding time to be 2 hours, raising the temperature of the kettle to 130-140 ℃ after the dropwise adding is finished, and continuously stirring for 2-4 hours. Sampling and detecting, when the content of phenol is less than or equal to 0.5%, reducing the temperature of a reaction system to 15 ℃, starting a stirrer and a heat and cold exchange all-in-one machine, slowly adding 150g of clear water to perform extraction and quenching to stop the reaction, and controlling the temperature of a reaction kettle to be less than 40 ℃ in the extraction and quenching process.
c) Transferring the generated p-tert-butylphenol reaction liquid to a separating funnel, and standing and layering for 0.5 h. The oil layer was placed in a beaker. Adding 100g of petroleum ether into the water layer, stirring for 0.5h, standing for layering, combining oil layers, putting into a beaker, and collecting the water layer into a waste liquid collecting barrel. 90g of 5% sodium hydroxide solution is metered into a beaker of the oil layer, a stirrer is started to carry out alkaline washing on the collected oil layer, the oil layer is stirred for 0.5h and then is kept stand for layering for 0.5h, and the alkaline solution layer is concentrated into a waste liquid collecting barrel. And adding 250g of clean water into the oil layer for washing, stirring for 0.5h, standing for layering for 0.5h, and washing twice. The oil layer is transferred to a hydrogenation reaction kettle, and the water layer is concentrated to a waste liquid collecting barrel.
d) Adding 5% palladium carbon catalyst into a hydrogenation reaction kettle according to a fixed amount, sealing the hydrogenation reaction kettle, replacing 4-6 times with nitrogen, then filling nitrogen to the pressure of 2.0Mpa, replacing 4-6 times with hydrogen after the system pressure is stable, then filling hydrogen, and adjusting the pressure of the hydrogenation reaction kettle to 2.0 Mpa. And (3) closing a hydrogen inlet valve after the system pressure is stable, heating to 80-150 ℃, opening the hydrogen valve after the reaction system pressure is balanced, and keeping the reaction pressure at 2.0Mpa for 5-10 h.
e) Sampling every 2h after 5h of reaction for chromatographic detection, and ending the reaction and relieving pressure when the content of the p-tert-butylphenol is less than or equal to 0.5 percent. Filtering the generated reaction liquid of the tert-butyl cyclohexanol, transferring the liquid phase filtrate into a rotary evaporator, cleaning the solid phase catalyst with petroleum ether, transferring into a hydrogenation reaction kettle, and carrying out the next batch of hydrogenation reaction.
f) And e) starting the rotary evaporator in the step e) to heat up, recovering petroleum ether at the normal pressure and the kettle temperature of 60-90 ℃, concentrating and recycling the collected petroleum ether, and transferring the bottom liquid of the bottle to a four-mouth flask.
g) 165g of acetic anhydride and 4g of p-toluenesulfonic acid are added into a four-neck flask in a metering mode, a stirrer is started, a heat and heat exchange all-in-one machine is started to heat, the reaction temperature is controlled to be 100-120 ℃, the reaction time is 3-5 hours, the reaction liquid is transferred into a rotary evaporator, acetic acid is recovered under normal pressure, and the bottom liquid of the flask is transferred into a beaker.
h) 35g of 5% sodium hydroxide solution is added into the beaker in a metered manner, the stirrer is started to carry out alkaline washing on the collected bottom liquid of the bottle, the bottom liquid is stirred for 0.5h and then is kept stand for layering for 0.5h, and the alkaline liquid layer is concentrated into a waste liquid collecting barrel. And adding 80g of clear water into the oil layer for washing, stirring for 0.5h, standing for layering for 0.5h, collecting the water layer into a waste liquid collecting barrel, and washing twice. Transferring the oil layer into a rotary evaporator, starting the rotary evaporator to heat, starting a vacuum pump, and collecting the irisquinolide to obtain 150.7g of the irisquinolide. The total yield is 76.1%.
The prepared iris ester is colorless transparent liquid, has sweet fragrance, fruit fragrance and rich costustoot and flower fragrance, and the purity of a product is 98.72 percent by gas chromatography analysis, wherein the cis-isomer accounts for 30.3 percent, the detected refractive index (20 ℃) is 1.4527, and the relative density (25 ℃) is 0.9383.
The foregoing shows and describes the general principles and broad features of the present invention and advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (8)
1. A synthetic method of iritate spice is characterized by comprising the following steps:
a) firstly, adding petroleum ether into a three-neck glass flask by weighing and metering, then adding anhydrous aluminum trichloride into the glass flask, starting a stirrer and a heat and cold exchange all-in-one machine, reducing the temperature of the glass flask to 10 to-15 ℃, slowly adding phenol into the glass flask, and continuing stirring for 0.5h after the feeding is finished;
b) continuously maintaining the temperature of the glass flask within 10 to-15 ℃, dropwise adding tert-butyl alcohol into the glass flask through a dropwise adding pump, controlling the dropwise adding time to be 2 hours, raising the temperature of the kettle to 120-140 ℃ after dropwise adding, and continuously stirring for 2-4 hours; sampling and carrying out chromatographic detection, when the content of phenol is less than or equal to 0.5%, reducing the temperature of a reaction system to 15 ℃, starting a stirrer and a heat and cold exchange all-in-one machine, slowly adding clear water to carry out extraction and quenching to stop the reaction, and controlling the temperature of a reaction kettle to be less than 40 ℃ in the extraction and quenching process;
c) transferring the generated p-tert-butylphenol reaction liquid to a separating funnel, standing and layering for 0.5h, putting an oil layer into a beaker, adding petroleum ether into a water layer, stirring for 0.5h, standing and layering, merging the oil layers, putting into the beaker, and concentrating the water layer into a waste liquid collecting barrel; adding 5% sodium hydroxide solution into a beaker of the oil layer, starting a stirrer to perform alkaline washing on the collected oil layer, stirring for 0.5h, standing and layering for 0.5h, and concentrating the alkaline solution layer into a waste liquid collecting barrel; adding clear water into the oil layer for washing, stirring for 0.5h, standing for layering for 0.5h, transferring the oil layer into a hydrogenation reaction kettle, and collecting the water layer into a waste liquid collecting barrel;
d) adding a 5% palladium-carbon catalyst into a hydrogenation reaction kettle in a fixed amount, sealing the hydrogenation reaction kettle, replacing the hydrogenation reaction kettle with nitrogen for 4-6 times, then filling the nitrogen to the pressure of 2.0Mpa, replacing the hydrogenation reaction kettle with hydrogen for 4-6 times after the system pressure is stable, then filling the hydrogen, and adjusting the pressure of the hydrogenation reaction kettle to 2.0 Mpa; closing a hydrogen inlet valve after the system pressure is stable, heating to 80-150 ℃, opening the hydrogen valve after the reaction system pressure is balanced, and keeping the reaction pressure at 2.0Mpa for 5-10 h;
e) sampling every 2h after 5h of reaction for chromatographic detection, ending the reaction when the content of the p-tert-butylphenol is less than or equal to 0.5 percent, and releasing pressure; filtering the generated reaction liquid of the tert-butyl cyclohexanol, transferring liquid phase filtrate into a rotary evaporator, cleaning a solid phase catalyst with petroleum ether, transferring the cleaned solid phase catalyst into a hydrogenation reaction kettle, and carrying out the next batch of hydrogenation reaction;
f) starting the rotary evaporator in the step e) to heat, recovering petroleum ether at normal pressure and at the kettle temperature of 60-90 ℃, concentrating and recycling the collected petroleum ether, and transferring the bottom liquid of the bottle to a four-neck flask;
g) adding acetic anhydride and p-toluenesulfonic acid into a four-neck flask in a metering manner, starting a stirrer, starting a heat and heat exchange all-in-one machine for heating, controlling the reaction temperature to be 100-120 ℃, reacting for 3-5 h, transferring the reaction liquid into a rotary evaporator, recovering acetic acid at normal pressure, and transferring the bottom liquid of the flask into a beaker;
h) adding 5% sodium hydroxide solution into a beaker in a metered manner, starting a stirrer to carry out alkali washing on the collected bottom liquid of the bottle, stirring for 0.5h, standing and layering for 0.5h, collecting an alkali liquid layer into a waste liquid collecting barrel, adding clear water into an oil layer for washing, stirring for 0.5h, standing and layering for 0.5h, collecting a water layer into the waste liquid collecting barrel, transferring the oil layer into a rotary evaporator, starting the rotary evaporator for heating, and starting a vacuum pump to collect irimate;
in the step a), the mass ratio of petroleum ether to phenol is preferably 2.0: 1-3.0: 1, and the molar ratio of aluminum trichloride to phenol is preferably 0.5: 1-1.0: 1; the molar ratio of tert-butanol to phenol in step b) is preferably 1.0:1 to 1.5: 1.
2. The process for the synthesis of iris ester fragrance according to claim 1, characterized in that: in the step c), the mass ratio of the petroleum ether to the water layer is 0.5: 1-2: 1, the mass ratio of the sodium hydroxide solution to the reaction liquid oil layer is 0.2: 1-2: 1, and the mass ratio of the clear water to the reaction liquid oil layer is 0.5: 1-2: 1.
3. The process for the synthesis of iris ester fragrance according to claim 2, characterized in that: the mass ratio of the petroleum ether to the water layer in the step c) is preferably 0.5: 1-1: 1, and the mass ratio of the sodium hydroxide solution to the reaction liquid oil layer is preferably 0.2: 1-1: 1; the mass ratio of the clean water to the reaction liquid oil layer is preferably 0.5: 1-1: 1.
4. The process for the synthesis of iris ester fragrance according to claim 1, characterized in that: the material of the hydrogenation reaction kettle in the step d) is stainless steel, and the design pressure is 0-5 MPa.
5. The process for the synthesis of iris ester fragrance according to claim 1, characterized in that: the molar ratio of acetic anhydride to p-tert-butylcyclohexanol in the step g) is 1.0: 1-5.0: 1, and the amount of p-toluenesulfonic acid is 0.5-5 wt% of the total amount of the p-toluenesulfonic acid.
6. The process for the synthesis of iris ester fragrance according to claim 5, characterized in that: the molar ratio of acetic anhydride to p-tert-butylcyclohexanol in the step g) is preferably 1.5: 1-2.0: 1, and the amount of p-toluenesulfonic acid is preferably 1.0-2.0 wt% of the total amount of the p-toluenesulfonic acid.
7. The process for the synthesis of iris ester fragrance according to claim 1, characterized in that: in the step h), the mass ratio of the 5% sodium hydroxide solution to the bottle bottom liquid is 0.2: 1-2: 1, and the mass ratio of the clear water to the oil layer is 0.5: 1-2: 1.
8. The process for the synthesis of iris ester fragrance according to claim 7, characterized by: in the step h), the mass ratio of the 5% sodium hydroxide solution to the bottle bottom liquid is preferably 0.2: 1-1: 1, and the mass ratio of the clear water to the oil layer is preferably 0.5: 1-1: 1.
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| JP3528519B2 (en) * | 1997-06-27 | 2004-05-17 | 住友化学工業株式会社 | Method for producing 4-t-butylcyclohexanol and method for producing 4-t-butylcyclohexyl acetate using the same |
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