CN108017518B - 1, 3-diphenyl-1-propanol and preparation method thereof - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/73—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation
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Abstract
1, 3-diphenyl-1-propanol and a preparation method thereof, relating to the technical field of chemical synthesis. The preparation method of the 1, 3-diphenyl-1-propanol provided by the invention comprises the following steps: benzaldehyde and acetophenone are subjected to catalytic reaction under the action of dibenzylamine trifluoroacetate and a catalyst to obtain 3-hydroxy-1, 3-diphenyl-1-acetone; carrying out a Huang Minlon reduction reaction on the 3-hydroxy-1, 3-diphenyl-1-acetone to obtain 1, 3-diphenyl-1-propanol; wherein the catalyst is L-proline or D-proline. The preparation method is simple to operate and low in cost, and can be used for preparing products with optical purity meeting requirements.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, and particularly relates to 1, 3-diphenyl-1-propanol and a preparation method thereof.
Background
1, 3-diphenyl-1-propanol and its derivatives are important chemical intermediates, which have wide application in medicine and agricultural chemicals, and can be used for preparing artificial immunosuppressant, preventing and treating neurodegenerative diseases, anticoagulation, anti-abnormal proliferation, beta-secretase inhibition, antibiosis, HIV-1 protease inhibition and the like, so the synthesis of the compounds has been widely studied, and the preparation methods of 1, 3-diphenyl-1-propanol reported in the literature so far can be divided into the following classes:
1. by reduction of the corresponding ketone:
Synthesis，2007，24，3877-3885；
Monatshefte fur Chemie，2008，139(7)，793-798；
Tetrahedron Letters，2011，52(22)，2826-2829；
ChemCatChem，2017，9(10)，1744-1748；
Advanced Synthesis and Catalysis，2016，358(24)，400-4018；
Journal of the American Chemical Society，1993，115(22)，9925-9938；
Advanced Synthesis and Catalysis，2011，353(2-3)，495-500；
Organometallics，2012，31(11)，4241-4250；
Journal of the American Chemical Society，2012，134(40)，16856-16868；
2. by reduction of the corresponding enone to give:
WO2004/87629，2004，A1；
Journal of Catalysis，2013，307，55-61；
Journal of Molecular Catalysis B：Enzymatic，2013，98，55-61；
3. by enol reduction to give:
Advanced Synthesis and Catalysis，2016，358(24)，4006-4018；
4. reacting phenylboronic acid with phenylpropyl aldehyde to obtain:
Letters in Organic Chemistry，2014，11(5)，356-360；
5. the benzyl Grignard reagent reacts with optical alcohol styrene oxide to obtain:
Journal of the American Chemical Society，2016，138(9)，3002-3011；
6. reacting zinc diphenyl with phenylpropyl aldehyde to obtain:
Journal of Organometallic Chemistry，2001，624(1-2)，157-161；
Angewandte Chemie-International Edition，2001，40(8)，1488-1490；
7. benzaldehyde reacts with a phenethyl Grignard reagent to obtain:
Journal of Organic Chemistry，2010，75(20)，6869-6878；
8. benzaldehyde reacts with diphenyl ethyl zinc to obtain:
Organic Process Research and Development，1998，2(1)，18-26；
9. reacting acetophenone with benzyl alcohol to obtain:
Advanced Synthesis and Catalysis，2016，358(24)，4006-4018；
10. splitting to obtain:
European Journal of Organic Chemistry，2013，29，6666-6676；
Journal of Organic Chemistry，2011，76(15)，6401-6406；
the methods listed above mostly use expensive chemical reagents, are of poor utility, and the resolution method is uneconomical.
In addition, the invention patent with the publication number of CN102146020B discloses a synthesis method of 1, 3-diphenyl-1-propanol compounds, which is obtained by adopting p-substituted 1-phenyl ethanol and p-substituted benzyl alcohol as raw materials for catalytic reaction.
Therefore, a preparation method of 1, 3-diphenyl-1-propanol, which has the advantages of simple operation, low cost and high purity of the produced product, is needed.
Disclosure of Invention
The invention aims to provide a preparation method of 1, 3-diphenyl-1-propanol, which has the advantages of simple operation and low cost.
Another object of the present invention is to provide 1, 3-diphenyl-1-propanol prepared by the above preparation method, which has the advantage of high purity.
The technical problem to be solved by the invention is realized by adopting the following technical scheme.
A method for preparing 1, 3-diphenyl-1-propanol, comprising the steps of:
benzaldehyde and acetophenone are subjected to catalytic reaction under the action of dibenzylamine trifluoroacetate and a catalyst to obtain 3-hydroxy-1, 3-diphenyl-1-acetone;
carrying out Huang Minlon reduction reaction on 3-hydroxy-1, 3-diphenyl-1-acetone to obtain 1, 3-diphenyl-1-propanol;
wherein the catalyst is L-proline or D-proline.
Further, in a preferred embodiment of the present invention, the mass ratio of benzaldehyde and acetophenone is 1: 0.9-1.1.
Further, in the preferred embodiment of the present invention, the mass ratio of benzaldehyde to catalyst is 1: 0.1-0.3.
Further, in a preferred embodiment of the present invention, the mass ratio of benzaldehyde and dibenzylamine trifluoroacetate is 1: 0.2-0.3.
Further, in the preferred embodiment of the present invention, the time for catalytic reaction is 24-48 h.
Further, in the preferred embodiment of the present invention, the catalytic reaction is carried out with stirring at 30 to 70 r/min.
Further, in the preferred embodiment of the present invention, the Huang Minlon reduction reaction is carried out by adding ethylene glycol, hydrazine hydrate and potassium hydroxide into 3-hydroxy-1, 3-diphenyl-1-propanone, stirring and heating for reaction, filtering, washing and drying.
Further, in the preferred embodiment of the present invention, the Huang Minlon reduction reaction is carried out by dissolving 3-hydroxy-1, 3-diphenyl-1-propanone in ethylene glycol, adding hydrazine hydrate, heating to 90-110 deg.C, reacting for 1.5-3h, stirring, adding potassium hydroxide, stopping heating, and reacting for 22-28 h.
Further, in a preferred embodiment of the present invention, the mass ratio of benzaldehyde, hydrazine hydrate and potassium hydroxide is 1: 8-10: 10-12.
The invention also provides the 1, 3-diphenyl-1-propanol prepared by the preparation method of the 1, 3-diphenyl-1-propanol.
The 1, 3-diphenyl-1-propanol and the preparation method thereof have the beneficial effects that: the preparation method of the 1, 3-diphenyl-1-propanol provided by the embodiment of the invention comprises the following steps: benzaldehyde and acetophenone are subjected to catalytic reaction under the action of dibenzylamine trifluoroacetate, L-proline or D-proline to obtain 3-hydroxy-1, 3-diphenyl-1-acetone; the 3-hydroxy-1, 3-diphenyl-1-acetone is subjected to Huang Minlon reduction reaction to obtain the 1, 3-diphenyl-1-propanol. The preparation method is simple to operate and low in cost, and can be used for preparing products with optical purity meeting requirements.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The following is a detailed description of 1, 3-diphenyl-1-propanol and a method for preparing the same according to examples of the present invention.
A method for preparing 1, 3-diphenyl-1-propanol, comprising the steps of:
benzaldehyde and acetophenone are subjected to catalytic reaction under the action of dibenzylamine trifluoroacetate and a catalyst to obtain 3-hydroxy-1, 3-diphenyl-1-acetone; wherein the catalyst is L-proline or D-proline; preferably, dibenzylamine trifluoroacetate is added when benzaldehyde and acetophenone are catalytically reacted. More preferably, the mass ratio of benzaldehyde to acetophenone is 1: 0.9-1.1; the mass ratio of benzaldehyde to catalyst is 1: 0.1-0.3; the mass ratio of benzaldehyde to dibenzylamine trifluoroacetate was 1: 0.2 to 0.3; the time of catalytic reaction is 24-48 h; preferably, the catalytic reaction is carried out with stirring at 30-70 r/min.
The 3-hydroxy-1, 3-diphenyl-1-acetone is subjected to Huang Minlon reduction reaction to obtain the 1, 3-diphenyl-1-propanol. Preferably, the Huang Minlon reduction reaction is that ethylene glycol, hydrazine hydrate and potassium hydroxide are added into 3-hydroxy-1, 3-diphenyl-1-acetone, stirred and heated for reaction, and then filtered, washed and dried; more preferably, during the Huang Minlon reduction reaction, 3-hydroxy-1, 3-diphenyl-1-acetone is firstly dissolved in ethylene glycol, then hydrazine hydrate is added and heated to 90-110 ℃ for reaction for 1.5-3h, then the mixture is stirred and potassium hydroxide is added, and the heating and stirring reaction is stopped for 22-28 h; further preferably, the mass ratio of benzaldehyde, hydrazine hydrate and potassium hydroxide is 1: 8-10: 10-12.
The reaction equation of the specific preparation reaction is as follows, when L-proline is used as the catalyst:
alternatively, when D-proline is used as the catalyst:
the preparation method of 1, 3-diphenyl-1-propanol provided by the embodiment of the invention adopts low-cost L-proline or D-proline as an asymmetric synthesis catalyst, and dibenzylamine trifluoroacetate is used as a reaction additive, so that benzaldehyde and acetophenone can be catalytically synthesized to obtain 3-hydroxy-1, 3-diphenyl-1-acetone with higher purity, and research shows that the yield of the 3-hydroxy-1, 3-diphenyl-1-acetone obtained by adding dibenzylamine trifluoroacetate as the reaction additive reaches more than 80 percent, the purity of the product can reach more than 99 percent, and the yield and the purity of the 1, 3-diphenyl-1-propanol prepared by the Huang Minlon reduction reaction of the 3-hydroxy-1, 3-diphenyl-1-acetone are greatly improved. The preparation method of the 1, 3-diphenyl-1-propanol has the advantages that the raw materials are low in price and easy to obtain, the reaction process is mild, the operation process is simple, and the cheap catalyst and additive are adopted, so that the 1, 3-diphenyl-1-propanol with the optical purity meeting the requirement can be prepared, wherein the (1R) -1, 3-diphenyl-1-propanol is prepared when the L-proline is used as the catalyst, and the (1S) -1, 3-diphenyl-1-propanol is prepared when the D-proline is used as the catalyst.
The invention also provides the 1, 3-diphenyl-1-propanol prepared by the preparation method of the 1, 3-diphenyl-1-propanol, and the 1, 3-diphenyl-1-propanol has the advantage of high purity.
The features and properties of the present invention are described in further detail below with reference to examples.
Example 1
The embodiment provides a preparation method of 1, 3-diphenyl-1-propanol, which comprises the following specific steps:
s11, preparation of 3-hydroxy-1, 3-diphenyl-1-propanone: dissolving 1.2g of acetophenone (10mmol) and 1.06g of benzaldehyde (10mmol) in 80ml of anhydrous dimethyl sulfoxide, stirring uniformly at room temperature (25 ℃), adding 230 mgL-proline (2mmol) in one step, then adding 555mg of dibenzyl trifluoroacetate (2.06mmol), stirring at 30r/min for 48h at room temperature (25 ℃), then adding equivalent saturated ammonium chloride aqueous solution and ethyl acetate, extracting an inorganic layer with ethyl acetate, combining organic layers, drying with anhydrous magnesium sulfate, and concentrating to obtain a crude product of 3-hydroxy-1, 3-diphenyl-1-acetone.
S12, preparing (1S) -1, 3-diphenyl-1-propanol, dissolving the crude product of the 3-hydroxy-1, 3-diphenyl-1-acetone in 26ml of ethylene glycol, adding 3ml of hydrazine hydrate (100mmol), heating to 100 ℃ under stirring, preserving heat for 2h, adding 6g of potassium hydroxide (107mmol) while stirring, removing external heating, continuing stirring for 24 h, cooling with ice water, filtering, collecting solid, dissolving the solid in 40ml of dichloromethane, washing with 1N hydrochloric acid, 10 mass percent sodium bicarbonate water solution and saturated sodium chloride respectively, drying with anhydrous magnesium sulfate, concentrating, and performing column chromatography to obtain (1S) -1, 3-diphenyl-1-propanol.
The total yield of the two steps is counted to be 50%, the purity is over 80%, and the hydrogen nuclear magnetic spectrum and the optical rotation are consistent with the literature, so that the obtained finished product is (1S) -1, 3-diphenyl-1-propanol.
Example 2
The embodiment provides a preparation method of 1, 3-diphenyl-1-propanol, which comprises the following specific steps:
s21, preparation of 3-hydroxy-1, 3-diphenyl-1-propanone: dissolving 1.8g of acetophenone (15mmol) and 1.6g of benzaldehyde (15mmol) in 120ml of anhydrous dimethyl sulfoxide, stirring uniformly at room temperature (25 ℃), adding 230 mgD-proline (2mmol) in one step, then adding 555mg of dibenzyl trifluoroacetate (2.06mmol), stirring at 50r/min for 48h at room temperature (25 ℃), then adding equal amounts of saturated aqueous ammonium chloride solution and ethyl acetate, extracting an inorganic layer with ethyl acetate, combining organic layers, drying with anhydrous magnesium sulfate, and concentrating to obtain a crude product of 3-hydroxy-1, 3-diphenyl-1-acetone.
S22, preparing (1R) -1, 3-diphenyl-1-propanol, dissolving the crude product of the 3-hydroxy-1, 3-diphenyl-1-acetone in 35ml of ethylene glycol, adding 4.5ml of hydrazine hydrate (150mmol), heating to 100 ℃ under stirring, preserving heat for 2h, adding 9g of potassium hydroxide (160mmol) while stirring, removing external heating, continuing stirring for 24 h, cooling with ice water, filtering, collecting solid, dissolving the solid in 40ml of dichloromethane, washing with 1N hydrochloric acid, 10% sodium bicarbonate water solution and saturated sodium chloride respectively, drying with anhydrous magnesium sulfate, concentrating, and separating by column chromatography to obtain (1R) -1, 3-diphenyl-1-propanol.
The total yield of the two steps is counted to be 56%, the purity is over 80%, and the hydrogen nuclear magnetic spectrum and the optical rotation are consistent with the literature, so that the obtained finished product is (1R) -1, 3-diphenyl-1-propanol.
Example 3
The embodiment provides a preparation method of 1, 3-diphenyl-1-propanol, which comprises the following specific steps:
s31, preparation of 3-hydroxy-1, 3-diphenyl-1-propanone: dissolving 2.4g of acetophenone (20mmol) and 2.12g of benzaldehyde (20mmol) in 150ml of anhydrous dimethyl sulfoxide, stirring uniformly at room temperature (25 ℃), adding 230 mgL-proline (2mmol) in one step, then adding 555mg of dibenzyl trifluoroacetate (2.06mmol), stirring at 70r/min for 48h at room temperature (25 ℃), then adding equivalent saturated ammonium chloride aqueous solution and ethyl acetate, extracting an inorganic layer with ethyl acetate, combining organic layers, drying with anhydrous magnesium sulfate, and concentrating to obtain a crude product of 3-hydroxy-1, 3-diphenyl-1-acetone.
S32, preparing (1S) -1, 3-diphenyl-1-propanol, dissolving the crude product of the 3-hydroxy-1, 3-diphenyl-1-acetone in 40ml of ethylene glycol, adding 6ml of hydrazine hydrate (200mmol), heating to 110 ℃ under stirring, preserving heat for 2h, adding 12g of potassium hydroxide (214mmol) while stirring, removing external heating, continuing stirring for 26 h, cooling with ice water, filtering, collecting a solid, dissolving the solid in 60ml of dichloromethane, washing with 1N hydrochloric acid, 10 mass percent aqueous solution of sodium bicarbonate and saturated sodium chloride respectively, drying with anhydrous magnesium sulfate, concentrating, and performing column chromatography to obtain (1S) -1, 3-diphenyl-1-propanol.
The total yield of the two steps is counted to be 52%, the purity is over 80%, and the hydrogen nuclear magnetic spectrum and the optical rotation are consistent with the literature, so that the obtained finished product is (1S) -1, 3-diphenyl-1-propanol.
In conclusion, the preparation method of 1, 3-diphenyl-1-propanol provided by the embodiment of the invention has the advantages of cheap and easily available raw materials, mild reaction process, simple operation process, and cheap catalyst and additive, and can prepare 1, 3-diphenyl-1-propanol with optical purity meeting the requirement,
the embodiments described above are some, but not all embodiments of the invention. The detailed description of the embodiments of the present invention is not intended to limit the scope of the invention as claimed, but is merely representative of selected embodiments of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Claims (9)
1. A preparation method of 1, 3-diphenyl-1-propanol is characterized by comprising the following steps:
benzaldehyde and acetophenone are subjected to catalytic reaction under the action of dibenzylamine trifluoroacetate and a catalyst to obtain 3-hydroxy-1, 3-diphenyl-1-acetone;
carrying out a Huang Minlon reduction reaction on the 3-hydroxy-1, 3-diphenyl-1-acetone to obtain 1, 3-diphenyl-1-propanol;
wherein the catalyst is L-proline or D-proline.
2. The process for the preparation of 1, 3-diphenyl-1-propanol according to claim 1, characterized in that the mass ratio of the benzaldehyde and the acetophenone is 1: 0.9-1.1.
3. The process for the preparation of 1, 3-diphenyl-1-propanol according to claim 1, characterized in that the mass ratio of the benzaldehyde to the catalyst is 1: 0.1-0.3.
4. The process for the preparation of 1, 3-diphenyl-1-propanol according to claim 1, characterized in that the mass ratio of the benzaldehyde and dibenzylamine trifluoroacetate is 1: 0.2-0.3.
5. The process for the preparation of 1, 3-diphenyl-1-propanol according to claim 4, characterized in that the catalytic reaction time is 24-48 h.
6. The process for preparing 1, 3-diphenyl-1-propanol according to claim 1, wherein the catalytic reaction is carried out under stirring at 30-70 r/min.
7. The method for preparing 1, 3-diphenyl-1-propanol according to claim 1, wherein the Huang Minlon reduction reaction is carried out by adding ethylene glycol, hydrazine hydrate and potassium hydroxide into 3-hydroxy-1, 3-diphenyl-1-propanone, stirring, heating for reaction, filtering, washing and drying.
8. The method for preparing 1, 3-diphenyl-1-propanol according to claim 7, wherein the Huang Minlon reduction reaction is carried out by dissolving 3-hydroxy-1, 3-diphenyl-1-propanone in the ethylene glycol, adding hydrazine hydrate, heating to 90-110 ℃ for reaction for 1.5-3h, stirring, adding potassium hydroxide and stopping heating and stirring for reaction for 22-28 h.
9. The method for producing 1, 3-diphenyl-1-propanol according to claim 7, wherein the mass ratio of the benzaldehyde, the hydrazine hydrate and the potassium hydroxide is 1: 8-10: 10-12.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1253941A (en) * | 1998-10-16 | 2000-05-24 | Basf公司 | Preparation method of substituted dibenzoyl methane compound |
| CN102146020A (en) * | 2010-02-10 | 2011-08-10 | 吉林大学 | Method for synthesizing 1,3-diphenyl-1-propanol compound |
| CN102924236A (en) * | 2012-10-30 | 2013-02-13 | 武汉怡兴化工有限公司 | Preparation method of diphenylmethanol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1253941A (en) * | 1998-10-16 | 2000-05-24 | Basf公司 | Preparation method of substituted dibenzoyl methane compound |
| CN102146020A (en) * | 2010-02-10 | 2011-08-10 | 吉林大学 | Method for synthesizing 1,3-diphenyl-1-propanol compound |
| CN102924236A (en) * | 2012-10-30 | 2013-02-13 | 武汉怡兴化工有限公司 | Preparation method of diphenylmethanol |
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