CN111018685B - Synthetic method of alpha-dihydrodamascone - Google Patents
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Abstract
The invention provides a method for synthesizing alpha-dihydrodamascone, which takes citranitrile as a raw material to generate alpha-pseudodamascone through one-step reaction, saves oxidants such as sodium dichromate or chromium sesquioxide, and has the advantages of good reaction environmental protection property, low raw material cost, mild operation conditions and short reaction period. The method generates the alpha-dihydrodamascone through three-step reaction, has short reaction route, greatly reduces the total synthesis time, greatly improves the yield, and is particularly suitable for industrial production and application.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthetic method of alpha-dihydrodamascone.
Background
The alpha-dihydrodamascone is a main fragrant substance of the Bagalia rose oil, has fine and pleasant rose fragrance, and contains various foreign high-grade perfumes and essences used by famous tobacco brands. At present, the following alpha-dihydrodamascone synthesis processes exist: 1. the alpha-ionone is taken as a raw material and is synthesized by 5 steps of reactions such as alpha-cyclohexene isoxazole, enaminone, diketone, hydroxyketone, alpha-dihydro damascone and the like, but the synthetic route has more steps, complicated operation and high danger degree of hydrogenation reaction twice. 2. The method takes citral as a starting material, and the citral is synthesized by 5 steps of reactions of huff base, alpha-cyclocitral, alpha-dihydro-isopulegone and alpha-dihydro-isopulegone, and has the defects of more steps and complicated operation, wherein sodium dichromate and other oxidants are needed for hydroxyl oxidation, and the environmental pollution is greater. 3. The method takes citral as a starting material, and the citral is synthesized by 4 steps of reactions of alpha-pseudoisopulegol, alpha-pseudoisopulegone, alpha-pseudodamascone and alpha-dihydrodamascone, and has the defects of more steps and complicated operation, wherein sodium dichromate and other oxidants are needed for hydroxyl oxidation, and the environmental pollution is greater. Therefore, the development of a novel synthetic method for α -dihydrodamascone has been the focus of research.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a synthetic method of alpha-dihydro damascone to solve the defects of overlong reaction route, low reaction yield and complex and dangerous reaction operation in the existing synthetic method of alpha-dihydro damascone.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows: a synthetic method of alpha-dihydrodamascone is carried out according to the following chemical formula:
specifically, the synthesis method comprises the following steps:
1) Sequentially adding magnesium particles and allyl chloride into an organic solvent, carrying out reflux reaction, then adding citranitrile at 0-5 ℃, stirring again for reaction, then dripping deionized water at 0-10 ℃, adjusting the pH value by using hydrochloric acid (65126), 6-7, standing for layering, separating a water phase and an organic phase, then using a first solvent to extract substances in the water phase, combining the first solvent after the water phase is extracted with the organic phase, concentrating, and carrying out reduced pressure distillation and refining to obtain an intermediate I;
2) Stirring and dissolving potassium hydroxide in tert-butyl alcohol, adding the intermediate I obtained in the step 1, controlling the temperature to be 30-50 ℃, stirring and reacting, neutralizing with acetic acid until the pH value is 651266-7, evaporating to remove tert-butyl alcohol, extracting residual liquid with a second solvent, concentrating the extracted second solvent, and performing reduced pressure rectification to obtain an intermediate II;
3) Anhydrous SnCl 4 Stirring and dissolving in benzene, adding the intermediate II obtained in the step 2, stirring and reacting at room temperature, then controlling the temperature to be 0-5 ℃, adding deionized water, neutralizing with sodium bicarbonate solution until the pH value reaches 651261261266-7, standing and layering, separating, extracting the water phase with a third solvent, concentrating the third solvent after extracting the water phase, and carrying out reduced pressure rectification to obtain the target product alpha-dihydrodamascone.
On the basis of the technical scheme, the invention can further have the following specific selection or optimized selection.
Specifically, in the step 1), the ratio of the amount of the magnesium particles, the allyl chloride and the citraconite is 1-2. The time of the reflux reaction is 1-2 hours, the time of the stirring reaction is 1-2 hours, and the temperature for concentrating the organic phase and the first solvent is 85 ℃. The intermediate I obtained in the step 1) is 6, 10-dimethyl-1, 5, 9-undecatrien-4-ketone, the purity of the intermediate is more than 90%, and the yield of the intermediate is more than 70%.
Specifically, the dosage of the potassium hydroxide and the intermediate I in the step 2) is 1 to 20-30 mass percent, and the dosage of the intermediate I and the tertiary butanol is 1 g. The stirring reaction time is 1-2 hours, and the second solvent used for extraction is diethyl ether. The intermediate II obtained in the step 2) is 6, 10-dimethyl-2, 5, 9-undecatrien-4-one, the purity of the intermediate is more than 90%, and the yield of the intermediate is more than 70%.
Specifically, the anhydrous SnCl in the step 3) 4 The dosage of the intermediate II and the intermediate II is 1-20 by mass, and the dosage of the intermediate II and the benzene is 1g by volume massml, the concentration of the sodium bicarbonate solution is 10wt%. The stirring reaction time is 3-5 hours, the third solvent used for extraction is diethyl ether, and extraction is carried out for three times. The purity of the alpha-dihydro damascone obtained in the step 3) is more than 98%, and the yield is more than 60%.
Compared with the prior art, the invention has the beneficial effects that: the synthesis method of alpha-dihydrodamascone provided by the invention takes the citraconite as the raw material, generates the alpha-pseudodamascone through one-step reaction, saves oxidants such as sodium dichromate or chromium sesquioxide, and has the advantages of good reaction environmental protection property, low raw material cost, mild operation conditions, high reaction yield and short reaction period. The method generates the alpha-dihydro damascone through three steps of reactions, has short reaction route, greatly reduces the total synthesis time, greatly improves the yield, and is particularly suitable for industrial production and application.
Detailed Description
For better understanding of the present invention, the following examples are provided to further illustrate the present invention, but the present invention is not limited to the following examples.
The invention provides a synthetic method of alpha-dihydro damascone, which comprises the following reaction according to the chemical formula:
specifically, the synthesis method comprises the following steps:
1) Sequentially adding magnesium particles and allyl chloride into an organic solvent, carrying out reflux reaction, then adding citranitrile at 0-5 ℃, stirring again for reaction, then dripping deionized water at 0-10 ℃, adjusting the pH value by using hydrochloric acid (65126), 6-7, standing for layering, separating a water phase and an organic phase, then using a first solvent to extract substances in the water phase, combining the first solvent after the water phase is extracted with the organic phase, concentrating, and carrying out reduced pressure distillation and refining to obtain an intermediate I;
2) Potassium hydroxide is stirred and dissolved in tert-butyl alcohol, then the intermediate I obtained in the step 1 is added, after the temperature is controlled to be 30-50 ℃ and stirring reaction is finished, acetic acid is used for neutralizing until the pH value reaches 65126, 6-7, tert-butyl alcohol is evaporated, a second solvent is used for extracting residual liquid, then the extracted second solvent is concentrated and then the reduced pressure rectification is carried out to obtain an intermediate II;
3) Anhydrous SnCl 4 Stirring and dissolving the mixture in benzene, adding the intermediate II obtained in the step (2), stirring and reacting at room temperature, then controlling the temperature to be 0-5 ℃, adding deionized water, neutralizing the mixture by using a sodium bicarbonate solution until the pH value is 65126, 6-7, standing and layering, separating, extracting an aqueous phase by using a third solvent, concentrating the third solvent after extracting the aqueous phase, and carrying out reduced pressure rectification to obtain the target product alpha-dihydrodamascone.
On the basis of the technical scheme, the invention can further have the following specific selection or optimized selection.
Specifically, in the step 1), the ratio of the amount of the magnesium particles, the allyl chloride and the citraconite is 1-3. The time of the reflux reaction is 1-2 hours, the time of the stirring reaction is 1-2 hours, and the temperature for concentrating the organic phase and the first solvent is 85 ℃. The intermediate I obtained in the step 1) is 6, 10-dimethyl-1, 5, 9-undecatrien-4-ketone, the purity of the intermediate is more than 90%, and the yield of the intermediate is more than 70%.
Specifically, the dosage of the potassium hydroxide and the intermediate I in the step 2) is 1 to 20-30 mass percent, and the dosage of the intermediate I and the tertiary butanol is 1 g. The stirring reaction time is 1-2 hours, and the second solvent used for extraction is diethyl ether. The intermediate II obtained in the step 2) is 6, 10-dimethyl-2, 5, 9-undecatrien-4-one, the purity of the intermediate is more than 90%, and the yield of the intermediate is more than 70%.
Specifically, the anhydrous SnCl in the step 3) 4 The mass ratio of the intermediate II to the benzene is 1 to 20, the mass ratio of the intermediate II to the benzene is 1gThe concentration of the sodium bicarbonate solution was 10wt%. The stirring reaction time is 3-5 hours, the third solvent used for extraction is diethyl ether, and extraction is carried out for three times. The purity of the alpha-dihydrodamascone obtained in the step 3) is more than 98%, and the yield is more than 60%.
Example 1:
1) Adding 15g of magnesium particles and 100ml of anhydrous ether into a 1000ml three-necked bottle, adding a mixed solution of 22g of allyl chloride and 200ml of anhydrous ether dropwise while stirring, and refluxing for 1 hour after dropwise adding; then the temperature is controlled between 0 ℃ and 5 ℃, mixed solution of 28g of citral and 50ml of anhydrous ether is dripped, stirring reaction is continued for 1 hour after dripping, then 100ml of water is dripped for hydrolysis at the temperature between 0 ℃ and 10 ℃, hydrochloric acid is used for regulating the pH value to 651267, the mixture is 6 to 7, standing and layering are carried out, 50ml of ether is used for extraction of water phase, organic phases are combined and concentrated to 85 ℃ to obtain crude product, the crude product is decompressed and refined to obtain the 6, 10-dimethyl-1, 5, 9-undecatrien-4-one, the purity is about 93 percent, and the yield is about 71 percent.
2) Adding 100ml of tert-butyl alcohol and 1g of potassium hydroxide into a 250ml three-neck flask, stirring for dissolving, then adding 22g of the synthesized ketone in the previous step, controlling the temperature to be 30-50 ℃, stirring for reacting for about 1 hour, neutralizing the solution to PH by acetic acid, 651267, 6-7, evaporating the solvent, extracting the residual liquid by diethyl ether, concentrating, and then carrying out reduced pressure rectification to obtain the 6, 10-dimethyl-2, 5, 9-undecatrien-4-one with the purity of about 91% and the yield of about 78%.
3) About 100ml of benzene and anhydrous SnCl are added into a 250ml three-neck flask 4 About 1g, stirring for dissolving, then adding about 18g of the synthesized ketone, stirring for reacting for about 3-5 hours at room temperature, controlling the temperature to be 0-5 ℃, adding about 30ml of water, neutralizing to PH value of 651266-7 by using 10% sodium bicarbonate solution, standing for layering, extracting the water phase for 3 times by using ethyl ether, concentrating the organic phase, and performing reduced pressure rectification to obtain the alpha-dihydrodamascone with the purity of about 98% and the yield of about 62%.
Example 2:
1) Adding 10g of magnesium particles and 80ml of anhydrous ether into a 1000ml three-necked bottle, adding a mixed solution of 20g of allyl chloride and 80ml of anhydrous ether dropwise while stirring, and refluxing for 2 hours after dropwise addition; then the temperature is controlled between 0 and 5 ℃, mixed liquid of 20g of citral and 40ml of anhydrous ether is dripped, the mixture is continuously stirred and reacts for 1 hour after dripping, then 100ml of water is dripped for hydrolysis at the temperature of between 0 and 10 ℃, hydrochloric acid is used for regulating the pH value to 651266, the mixture is kept stand and layered, 50ml of ether is used for extracting a water phase, organic phases are combined and concentrated to 85 ℃ to obtain a crude product, the crude product is decompressed and refined to obtain the 6, 10-dimethyl-1, 5, 9-undecatrien-4-one, the purity is about 95 percent, and the yield is about 73 percent.
2) Adding about 80ml of tert-butyl alcohol and about 1g of potassium hydroxide into a 250ml three-neck flask, stirring for dissolving, then adding 20g of the synthesized ketone in the previous step, controlling the temperature to be 30-50 ℃, stirring for reacting for about 2 hours, neutralizing with acetic acid until the pH value is adjusted to 651267, evaporating to remove the solvent, extracting the residual liquid with diethyl ether, concentrating, and then carrying out reduced pressure rectification to obtain the 6, 10-dimethyl-2, 5, 9-undecatrien-4-one with the purity of about 93% and the yield of about 75%.
3) About 80ml of benzene and anhydrous SnCl are added into a 250ml three-neck flask 4 Stirring to dissolve about 1g, adding about 20g of the synthesized ketone, stirring to react for about 5 hours at room temperature, controlling the temperature to be 0-5 ℃, adding about 20ml of water, neutralizing with 10% sodium bicarbonate solution by mass fraction to PH =7, standing for layering, extracting the water phase with diethyl ether for 3 times, concentrating the organic phase, and performing reduced pressure rectification to obtain the alpha-dihydrodamascone with the purity of about 98.3% and the yield of about 66%.
Example 3:
1) Adding 17g of magnesium particles and 200ml of anhydrous ether into a 1000ml three-necked bottle, adding a mixed solution of 25g of allyl chloride and 80ml of anhydrous ether dropwise while stirring, and refluxing for 2 hours after dropwise addition; then the temperature is controlled between 0 and 5 ℃, 30g of mixed solution of the citrates and 80ml of anhydrous ether is dripped, the mixture is continuously stirred and reacts for 2 hours after dripping, then 100ml of water is dripped for hydrolysis after the temperature is controlled between 0 and 10 ℃, the pH value is adjusted to 651267 by hydrochloric acid, the mixture is kept stand and layered, the water phase is extracted by 50ml of ether, the organic phases are merged and concentrated to 85 ℃ to obtain a crude product, the crude product is decompressed and refined to obtain the 6, 10-dimethyl-1, 5, 9-undecatrien-4-one, the purity is about 96 percent, and the yield is about 72 percent.
2) Adding about 100ml of tert-butyl alcohol and about 1g of potassium hydroxide into a 250ml three-neck flask, stirring for dissolving, then adding 25g of the synthetic ketone in the previous step, controlling the temperature to be 30-50 ℃, stirring for reacting for about 2 hours, neutralizing with acetic acid to pH value of 651267, evaporating to remove the solvent, extracting the residual liquid with diethyl ether, concentrating, and then carrying out reduced pressure rectification to obtain the 6, 10-dimethyl-2, 5, 9-undecatrien-4-one with the purity of about 95% and the yield of about 77%.
3) About 100ml of benzene and anhydrous SnCl are added into a 250ml three-neck flask 4 About 1g, stirring to dissolve, adding about 20g of the synthesized ketone, and stirring at room temperature to react for about 4 hoursWhen the temperature is controlled to be 0-5 ℃, about 50ml of water is added, 10% sodium bicarbonate solution is used for neutralizing until the pH value is increased, 651267, standing and layering are carried out, the water phase is extracted by ethyl ether for 3 times, the organic phase is concentrated, and the reduced pressure rectification is carried out, so that the alpha-dihydrodamascone with the purity of about 98.2% and the yield of about 66% is obtained.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (8)
1. A method for synthesizing alpha-dihydrodamascone is characterized in that the reaction is carried out according to the following chemical formula:
the synthesis method comprises the following steps:
1) Sequentially adding magnesium particles and allyl chloride into an organic solvent, carrying out reflux reaction, then adding citralonitrile at 0-5 ℃, stirring again for reaction, then dripping deionized water at 0-10 ℃, adjusting pH by using hydrochloric acid water (651265), 6-7, standing for layering, separating a water phase and an organic phase, then using a first solvent to extract substances in the water phase, combining and concentrating the first solvent after the water phase is extracted and the organic phase, and carrying out reduced pressure distillation and refining to obtain an intermediate I;
2) Stirring and dissolving potassium hydroxide in tert-butyl alcohol, adding the intermediate I obtained in the step 1, controlling the temperature to be 30-50 ℃, stirring and reacting, neutralizing with acetic acid until the pH value is 651266-7, evaporating to remove tert-butyl alcohol, extracting residual liquid with a second solvent, concentrating the extracted second solvent, and performing reduced pressure rectification to obtain an intermediate II;
3) Anhydrous SnCl 4 Stirring and dissolving the mixture in benzene, adding the intermediate II obtained in the step 2, stirring and reacting at room temperature, then adding deionized water at the temperature of 0-5 ℃, neutralizing the mixture by using a sodium bicarbonate solution until the pH value is 651266-7, standing and layering, separating, extracting an aqueous phase by using a third solvent, concentrating the third solvent after extracting the aqueous phase, and performing reduced pressure rectification to obtain a target product alpha-dihydrodamascone.
2. The method for synthesizing alpha-dihydrodamascone according to claim 1, characterized in that: in the step 1), the mass ratio of the magnesium particles, the allyl chloride and the citraconite is 1-2.
3. The method for synthesizing alpha-dihydrodamascone according to claim 1, characterized in that: the reflux reaction time in the step 1) is 1-2 hours, the stirring reaction time is 1-2 hours, and the temperature for concentrating the organic phase and the first solvent is 85 ℃.
4. The method for synthesizing alpha-dihydrodamascone according to claim 1, characterized in that: the intermediate I obtained in the step 1) is 6, 10-dimethyl-1, 5, 9-undecetrien-4-ketone, the purity of the intermediate is more than 90 percent, and the yield is more than 70 percent.
5. The method for synthesizing alpha-dihydrodamascone according to any one of claims 2 to 4, characterized in that: in the step 2), the using amounts of the potassium hydroxide and the intermediate I are 1-30 by mass, the using amounts of the intermediate I and the tert-butanol are 1g to 2-5ml by volume mass ratio, the stirring reaction time is 1-2 hours, and the second solvent used for extraction is diethyl ether.
6. The method for synthesizing alpha-dihydrodamascone according to any one of claims 2 to 4, characterized in that: the intermediate II obtained in the step 2) is 6, 10-dimethyl-2, 5, 9-undecetrien-4-ketone, the purity of the intermediate II is more than 90%, and the yield of the intermediate II is more than 70%.
7. The method for synthesizing alpha-dihydrodamascone according to any one of claims 2 to 4, characterized in that: anhydrous SnCl in step 3) 4 The mass ratio of the intermediate II to the benzene is 1g to 15-20, the concentration of the sodium bicarbonate solution is 10wt%, the stirring reaction time is 3-5 hours, the third solvent used for extraction is diethyl ether, and the extraction is carried out for three times.
8. The method for synthesizing alpha-dihydrodamascone according to any one of claims 2 to 4, wherein the synthesis method comprises the following steps: the purity of the alpha-dihydrodamascone obtained in the step 3) is more than 98%, and the yield is more than 60%.
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH503685A (en) * | 1968-11-01 | 1971-02-28 | Firmenich & Cie | Unsaturated ketone prodn |
| US3931326A (en) * | 1967-11-09 | 1976-01-06 | Firmenich Sa | Alkenoyl-cyclohexadienes |
| CN1172099A (en) * | 1997-07-08 | 1998-02-04 | 云南省化工研究院 | Method for synthesizing dihydro turkone |
| CN101698636A (en) * | 2009-10-28 | 2010-04-28 | 上海应用技术学院 | Method for synthesizing beta-damascenone |
| CN102336636A (en) * | 2010-07-16 | 2012-02-01 | 上海爱普植物科技有限公司 | Method for synthesizing alkyl-substituted cyclohexenyl alpha, beta-saturated ketones |
| CN103058841A (en) * | 2013-01-08 | 2013-04-24 | 河南师范大学 | Preparation method of alpha-damascenone perfume |
| CN108558623A (en) * | 2018-05-28 | 2018-09-21 | 辽宁科技大学 | A kind of preparation process of α-damascenone |
| CN109053407A (en) * | 2018-06-28 | 2018-12-21 | 厦门欧米克生物科技有限公司 | A method of synthesis β-Damascenone |
| CN110002979A (en) * | 2019-01-22 | 2019-07-12 | 游翔 | A kind of preparation method of damascone |
-
2019
- 2019-12-30 CN CN201911398520.1A patent/CN111018685B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931326A (en) * | 1967-11-09 | 1976-01-06 | Firmenich Sa | Alkenoyl-cyclohexadienes |
| CH503685A (en) * | 1968-11-01 | 1971-02-28 | Firmenich & Cie | Unsaturated ketone prodn |
| CN1172099A (en) * | 1997-07-08 | 1998-02-04 | 云南省化工研究院 | Method for synthesizing dihydro turkone |
| CN101698636A (en) * | 2009-10-28 | 2010-04-28 | 上海应用技术学院 | Method for synthesizing beta-damascenone |
| CN102336636A (en) * | 2010-07-16 | 2012-02-01 | 上海爱普植物科技有限公司 | Method for synthesizing alkyl-substituted cyclohexenyl alpha, beta-saturated ketones |
| CN103058841A (en) * | 2013-01-08 | 2013-04-24 | 河南师范大学 | Preparation method of alpha-damascenone perfume |
| CN108558623A (en) * | 2018-05-28 | 2018-09-21 | 辽宁科技大学 | A kind of preparation process of α-damascenone |
| CN109053407A (en) * | 2018-06-28 | 2018-12-21 | 厦门欧米克生物科技有限公司 | A method of synthesis β-Damascenone |
| CN110002979A (en) * | 2019-01-22 | 2019-07-12 | 游翔 | A kind of preparation method of damascone |
Non-Patent Citations (2)
| Title |
|---|
| Diastereo-Divergent Synthesis of Saturated Azaheterocycles Enabled by tBuOK-Mediated Hydroamination of Alkenyl Hydrazones;Atsushi Kaga等;《Chem.Eur.J.2015》;20151231;第21卷;supporting information 化合物12b的合成 * |
| α-大马酮香料合成方法的改进;李卫明等;《化学试剂》;20061231;第28卷(第11期);实验部分 * |
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