CN103553894A - Synthetic method of 1, 3-diphenyl-1-acetone - Google Patents
Synthetic method of 1, 3-diphenyl-1-acetone Download PDFInfo
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- CN103553894A CN103553894A CN201310544768.0A CN201310544768A CN103553894A CN 103553894 A CN103553894 A CN 103553894A CN 201310544768 A CN201310544768 A CN 201310544768A CN 103553894 A CN103553894 A CN 103553894A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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Abstract
The invention relates to a synthetic method of 1, 3-diphenyl-1-acetone, belonging to the technical field of preparation of organic compounds. The synthetic method comprises the following steps: firstly, mixing a raw material 3-chloropropionylchloride with a Lewis acid catalyst; after heating, continuously dropping a mixed liquid of benzene and a the Lewis acid catalyst into a reaction system; after reaction, adding diluted hydrochloric acid; dividing liquor; concentrating; and then, carrying out recrystallization by ethanol to obtain a target product. The Lewis acid catalyst provided by the invention can be selected from one of aluminum trichloride, ferric trichloride and zinc chloride or a mixture of more than two of aluminum trichloride, ferric trichloride and zinc chloride. The dropping speed of the mixed liquid of the benzene and the Lewis acid catalyst is 1-5ml/min. Reduced pressure concentration is carried out at 40-60 DEG C, and distilled benzene is recycled. During recrystallization, 5-10ml of ethanol is added into the product per g. The synthetic method provided by the invention is low in production cost, mature in process, high in yield, simple to operate, high in purity of the product, good in quality and applicable to industrialized production.
Description
Technical field
The invention belongs to organic compound preparing technical field, relate in particular to a kind of 1, the synthetic method of 3-phenylbenzene-1-acetone.
Background technology
1,3-phenylbenzene-1-acetone claims again dihydrochalcone, ω-benzyl methyl phenyl ketone, beta-phenyl Propiophenone etc.1,3-phenylbenzene-1-acetone and derivative thereof are important chemical intermediates, are also a kind of important sweeting agents for food.Have been found that at present multiple dihydrochalcone glycoside all has very high sugariness, conventionally the 100-1000 that is equivalent to sucrose sweetness doubly, the 3-5 of asccharin doubly and nontoxicity, empty calory or low in calories, and sweet taste comes slowly, the aftertaste time length is long, sweet taste is salubrious and happy, can effectively reduce human body in beverage or pharmaceuticals may with the sensitivity of bitter taste, solvable in water, stable.Therefore it can be used as various types of foodstuff additive, also has good pharmacological action simultaneously, in important use medically, is mainly used in diabetes and obesity.Simultaneously also because such product sweetness is quite large, so the consumption in food is very little, generally only account for 1% or still less (conventionally only have 0.5%).
1,3-phenylbenzene-1-acetone is the simplest compound in dihydrochalcone analog derivative, and its synthetic method mainly contains three kinds at present.First method is to become benzylidene acetophenone with methyl phenyl ketone with benzaldehyde, and then carries out catalytic hydrogenation and obtain 1,3-phenylbenzene-1-acetone.Synthetic method is shown in document Nakanishi S; Shundo T, et al.Chem Lett, 1979,8:955-956; Ohta H, Konishi J, et al.Chem Lett, 1983,12:1895-1896; Yutaka N, Masanori Y, et al.J Org Chem, 1991,56:6720-6722 etc.This method is current the most frequently used method, and its cost is relatively cheap, and yield is higher.Technique is comparative maturity also.But the catalyzer that needs expensive catalytic hydrogenation; Second method is that styracin is carried out to catalytic hydrogenation, obtains 3-phenylpropionic acid, then obtains 1,3-phenylbenzene-1-acetone through Friedel-Crafts (paying-Ke) acylations.Synthetic method is shown in document Yamato T, Hideshima C, et al.Org Chem, 1991,56 (2): 3955-3957 etc.Although this method cost is lower, yield is also lower.The third method is benzyl chloride and methyl phenyl ketone to be carried out to coupling obtain 1,3-phenylbenzene-1-acetone.Synthetic method is shown in document Negishi E, Idacavage M.Tetrahedron Lett, 1979,10:845-848 etc.This method is only used a step, and method is simple, but cost compare is high, and technique is more complicated also, and practical application is fewer.
Summary of the invention
The present invention is intended to overcome the deficiencies in the prior art part and provides a kind of method simple, and with low cost, yield is high, 1 of suitability for industrialized production, the synthetic method of 3-phenylbenzene-1-acetone.
For solving the problems of the technologies described above, the present invention is achieved in that
A kind of 1, the synthetic method of 3-phenylbenzene-1-acetone, it mixes raw material 3-chlorpromazine chloride with lewis acid catalyst, after heating, continue to the mixed solution that drips benzene and lewis acid catalyst in this reaction system, after having reacted, add dilute hydrochloric acid, separatory, concentrated, then after ethyl alcohol recrystallization, obtain object product.
As a kind of preferred version, lewis acid catalyst of the present invention can be selected one or more the mixture in aluminum chloride, iron trichloride and zinc chloride.
Further, Heating temperature of the present invention is 50～80 ℃.
Further, the rate of addition of benzene of the present invention and lewis acid catalyst mixed solution is 1～5ml/min.
Further, after having reacted, to add the concentration of dilute hydrochloric acid be 1～3M in the present invention.
Further, the present invention is at 40～60 ℃, to carry out concentrating under reduced pressure in temperature, and the benzene recirculation steaming is used.
Further, during recrystallization of the present invention, every gram of product adds 5～10ml ethanol.
The present invention adopts benzene and 3-chlorpromazine chloride under lewis acid catalyst effect, one-step synthesis 1, and 3-phenylbenzene-1-acetone, the method is simple to operate, with low cost, and yield is higher, and suitability for industrialized is produced.Technical scheme is as follows:
The invention has the beneficial effects as follows; using cheap benzene and 3-chlorpromazine chloride is raw material, utilizes inexpensive Louis's acid as catalyst simultaneously, adds the method for benzene after employing; pay-Ke acylation reaction and pay-Ke alkylated reaction can be carried out simultaneously; thereby through a step, just can obtain 1,3-phenylbenzene-1-acetone, avoid polystep reaction; technological operation is simple; greatly having improved total recovery, reduced production cost, is a kind of method of applicable suitability for industrialized production.
Embodiment
Below in conjunction with embodiment, the invention will be further described.
Embodiment 1:
In there-necked flask, add aluminum chloride 5g, 3-chlorpromazine chloride 10g, stirs and is heated to 50 ℃, then drips the mixed solution of aluminum chloride 5g and benzene 30ml, and rate of addition is 1ml/min.Continue to stir 30min, add the dilute hydrochloric acid 50ml of 1M, then add benzene 50ml, static separatory, organic phase is concentrated, and the benzene steaming reclaims and uses.Obtain thick product 15g, use 100ml ethyl alcohol recrystallization, obtain product 1,3-phenylbenzene-1-acetone 13g, productive rate 78%(calculates with 3-chlorpromazine chloride).
Embodiment 2:
In there-necked flask, add iron trichloride 5g, 3-chlorpromazine chloride 10g, stirs and is heated to 70 ℃, then drips the mixed solution of iron trichloride 5g and benzene 30ml, and rate of addition is 2ml/min.Continue to stir 30min, add the dilute hydrochloric acid 50ml of 3M, then add benzene 50ml, static separatory, organic phase is concentrated, and the benzene steaming reclaims and uses.Obtain thick product 14g, use 100ml ethyl alcohol recrystallization, obtain product 1,3-phenylbenzene-1-acetone 12g, productive rate 73%(calculates with 3-chlorpromazine chloride).
Embodiment 3:
In there-necked flask, add aluminum chloride 3g, zinc chloride 3g, 3-chlorpromazine chloride 10g, stirs and is heated to 80 ℃, then drips the mixed solution of aluminum chloride 5g and benzene 30ml, and rate of addition is 5ml/min.Continue to stir 30min, add the dilute hydrochloric acid 50ml of 1M, then add benzene 50ml, static separatory, organic phase is concentrated, and the benzene steaming reclaims and uses.Obtain thick product 16g, use 100ml ethyl alcohol recrystallization, obtain product 1,3-phenylbenzene-1-acetone 13.5g, productive rate 82%(calculates with 3-chlorpromazine chloride).
Embodiment 4:
In there-necked flask, add iron trichloride 3g, zinc chloride 3g, 3-chlorpromazine chloride 10g, stirs and is heated to 80 ℃, then drips the mixed solution of aluminum chloride 5g and benzene 30ml, and rate of addition is 5ml/min.Continue to stir 30min, add the dilute hydrochloric acid 50ml of 3M, then add benzene 50ml, static separatory, organic phase is concentrated, and the benzene steaming reclaims and uses.Obtain thick product 16g, use 100ml ethyl alcohol recrystallization, obtain product 1,3-phenylbenzene-1-acetone 11.5g, productive rate 70.1%(calculates with 3-chlorpromazine chloride).
The foregoing is only the preferred embodiments of the present invention, be not limited to the present invention, for a person skilled in the art, the present invention can have various modifications and variations.Within the spirit and principles in the present invention all, any modification of doing, be equal to replacement, improvement etc., within all should being included in protection scope of the present invention.
Claims (7)
1. one kind 1, the synthetic method of 3-phenylbenzene-1-acetone, it is characterized in that: raw material 3-chlorpromazine chloride is mixed with lewis acid catalyst, after heating, continue to the mixed solution that drips benzene and lewis acid catalyst in this reaction system, after having reacted, add dilute hydrochloric acid, separatory, concentrated, then after ethyl alcohol recrystallization, obtain target product.
2. according to claim 11, the synthetic method of 3-phenylbenzene-1-acetone, is characterized in that: described lewis acid catalyst is one or more the mixture in aluminum chloride, iron trichloride and zinc chloride.
3. according to claim 11, the synthetic method of 3-phenylbenzene-1-acetone, is characterized in that: Heating temperature is 50～80 ℃.
4. arbitrary described 1 according to claim 1～3, the synthetic method of 3-phenylbenzene-1-acetone, is characterized in that: under temperature of reaction, the rate of addition of benzene and lewis acid catalyst mixed solution is 1～5ml/min.
5. according to claim 41, the synthetic method of 3-phenylbenzene-1-acetone, is characterized in that: the concentration that adds dilute hydrochloric acid after having reacted is 1～3M.
6. according to claim 51, the synthetic method of 3-phenylbenzene-1-acetone, is characterized in that: in temperature, be at 40～60 ℃, to carry out concentrating under reduced pressure, the benzene recirculation steaming is used.
7. according to claim 61, the synthetic method of 3-phenylbenzene-1-acetone, is characterized in that: during recrystallization, every gram of product adds 5～10ml ethanol.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366000A (en) * | 2016-08-30 | 2017-02-01 | 枣阳凤泽精细化工有限公司 | Preparation method of 2-chloro-5-nitrobenzophenone |
| CN106397156A (en) * | 2016-08-30 | 2017-02-15 | 枣阳凤泽精细化工有限公司 | Preparation method of 2-chloro-benzophenone |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1305743A (en) * | 2000-12-27 | 2001-08-01 | 中国科学院广州化学研究所 | Process for synthesizing dihydrochalcone-type sweetening agent |
| WO2012098134A1 (en) * | 2011-01-18 | 2012-07-26 | Pierre Fabre Dermo-Cosmetique | Monoterpene derivatives of chalcone or dihydrochalcone and their use as depigmenting agents |
| CN102659539A (en) * | 2012-05-15 | 2012-09-12 | 北京化工大学 | Method for preparing dihydro-chalcones compounds by alpha, beta-unsaturated acyl chloride |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1305743A (en) * | 2000-12-27 | 2001-08-01 | 中国科学院广州化学研究所 | Process for synthesizing dihydrochalcone-type sweetening agent |
| WO2012098134A1 (en) * | 2011-01-18 | 2012-07-26 | Pierre Fabre Dermo-Cosmetique | Monoterpene derivatives of chalcone or dihydrochalcone and their use as depigmenting agents |
| CN102659539A (en) * | 2012-05-15 | 2012-09-12 | 北京化工大学 | Method for preparing dihydro-chalcones compounds by alpha, beta-unsaturated acyl chloride |
Non-Patent Citations (1)
| Title |
|---|
| 周阳: "由苯和不饱和酰氯通过串联付克反应合成二氢查尔酮类化合物", 《北京化工大学硕士研究生学位论文》, 15 October 2012 (2012-10-15), pages 22 - 25 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366000A (en) * | 2016-08-30 | 2017-02-01 | 枣阳凤泽精细化工有限公司 | Preparation method of 2-chloro-5-nitrobenzophenone |
| CN106397156A (en) * | 2016-08-30 | 2017-02-15 | 枣阳凤泽精细化工有限公司 | Preparation method of 2-chloro-benzophenone |
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