CN104529732A - Preparation method for 2,6-dibenzylidenecyclohexanone - Google Patents
Preparation method for 2,6-dibenzylidenecyclohexanone Download PDFInfo
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- CN104529732A CN104529732A CN201410748520.0A CN201410748520A CN104529732A CN 104529732 A CN104529732 A CN 104529732A CN 201410748520 A CN201410748520 A CN 201410748520A CN 104529732 A CN104529732 A CN 104529732A
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- pentylcyclohexanone
- benzal
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- dibenzylidenecyclohexanone
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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
- C07C45/61—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
- C07C45/74—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 dehydration
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method for 2,6-dibenzylidenecyclohexanone. The preparation method comprises: adding a certain amount of 2,6-dimethylcyclohexanone, benzaldehyde and a catalyst into a 250 mL three-neck flask provided with a stirrer and a reflux condensing tube, heating to 180-230 DEG C and reacting for 40-60 min; and filtering, adding a methanol aqueous solution into the filtrate, and simultaneously putting in an ice bath and cooling for 20-30 min, performing pumping filtration on precipitated crystal and drying, so as to obtain 2,6-dibenzylidenecyclohexanone. The disclosed preparation method for 2,6-dibenzylidenecyclohexanone is short in technological flow, easily available in raw materials and convenient to operate, helps to shorten reaction time and reduce production cost, the obtained product is relatively high in purity and yield, industrialized production is convenient, the product purity reaches 99% or more, and the product yield can reach 73%.
Description
Technical field
The present invention relates to a kind of preparation method of pharmaceutical intermediate 2,6-bis-benzal pentylcyclohexanone, belong to pharmaceutical technology sectors.
Background technology
Vinylbenzene ketone and benzylidene alkyl ketone are generally as the intermediate of synthetic drugs as pyrazoline derivative, and 2,6-bis-benzal pentylcyclohexanone are again be widely used in the precursor that synthesis has bioactive pyridine derivate.Therefore its synthetic method be always research focus, be especially aromatic aldehyde and pimelinketone condensation reaction more researchist paid attention to.Usually this type of reaction is carried out in strong acid or strong alkali environment, but Cannizzaro reaction occurs sometimes thus productive rate is declined.For avoiding the generation of this side reaction, mixture, the Pd/C-(TMSCI of many new catalyst Ph (III) Porphyrin), BMPTO and phase-transfer catalyst etc. used.Many novel reaction conditions are also used, as in ionic liquid, Ultrasonic Radiation and microwave condition etc., its reaction conditions is all harsher, is difficult to realize industrialization.
Summary of the invention
The object of this invention is to provide a kind of preparation method of 2,6-bis-benzal pentylcyclohexanone, the method is simple to operate, synthetic route is short, productive rate is higher.
The present invention is achieved through the following technical solutions: a kind of preparation method of 2,6-bis-benzal pentylcyclohexanone, comprises the steps:
In the 250 mL there-necked flasks that agitator and reflux condensing tube be housed, add a certain amount of 2,6-dimethylcyclohexanon, phenyl aldehyde and catalyzer, be heated to 180 ~ 230 DEG C of reaction 40 ~ 60min.Filter, in filtrate, add methanol solution, put into ice bath cooling 20 ~ 30min simultaneously, by the crystal suction filtration of separating out, dry, obtain 2,6-bis-benzal pentylcyclohexanone.
Further, 2,6-above-mentioned dimethylcyclohexanon, the mol ratio of phenyl aldehyde are 1:2.0 ~ 3.0.
Further, above-mentioned catalyzer is the vitriol oil and massfraction is the Pd/C of 10%.
Further, above-mentioned methanol solution volumetric concentration 50%.
2,6-bis-benzal pentylcyclohexanone preparation methods of the present invention, technical process is short, and raw material is easy to get, easy to operate, shorten the reaction times, reduce production cost, product purity and yield higher, be convenient to suitability for industrialized production, product purity reaches more than 99%, and product yield can reach 73%.
Embodiment
Set forth beneficial effect of the present invention further by the following examples:
Embodiment 1:
In the 250 mL there-necked flasks that agitator and reflux condensing tube are housed, add the vitriol oil of 12.6g 2,6-dimethylcyclohexanon, 21.2g phenyl aldehyde, 7.5g Pd/C and 150ml, be heated to 180 DEG C of reaction 40min.Filter, filtrate is put into ice bath cooling 20 ~ 30min, add methanol aqueous solution simultaneously, by the crystal suction filtration of separating out, dry, obtain 2,6-bis-benzal pentylcyclohexanone, product purity can reach 99.5%, and product yield can reach 71.6%.
Embodiment 2:
In the 250 mL there-necked flasks that agitator and reflux condensing tube are housed, add the vitriol oil of 12.6g 2,6-dimethylcyclohexanon, 21.2g phenyl aldehyde, 10g Pd/C and 150ml, be heated to 220 DEG C of reaction 60min.Filter, filtrate is put into ice bath cooling 20 ~ 30min, add methanol aqueous solution simultaneously, by the crystal suction filtration of separating out, dry, obtain 2,6-bis-benzal pentylcyclohexanone, product purity can reach 99.56%, and product yield can reach 72.7%.
Embodiment 3:
In the 250 mL there-necked flasks that agitator and reflux condensing tube are housed, add the vitriol oil of 12.6g 2,6-dimethylcyclohexanon, 31.8g phenyl aldehyde, 7.5g Pd/C and 150ml, be heated to 180 DEG C of reaction 40min.Filter, filtrate is put into ice bath cooling 20 ~ 30min, add methanol aqueous solution simultaneously, by the crystal suction filtration of separating out, dry, obtain 2,6-bis-benzal pentylcyclohexanone, product purity can reach 99.42%, and product yield can reach 70.5%.
Embodiment 4:
In the 250 mL there-necked flasks that agitator and reflux condensing tube are housed, add the vitriol oil of 12.6g 2,6-dimethylcyclohexanon, 31.8g phenyl aldehyde, 10g Pd/C and 150ml, be heated to 220 DEG C of reaction 60min.Filter, filtrate is put into ice bath cooling 20 ~ 30min, add methanol aqueous solution simultaneously, by the crystal suction filtration of separating out, dry, obtain 2,6-bis-benzal pentylcyclohexanone, obtain 2,6-bis-benzal pentylcyclohexanone, product purity can reach 99.51%, and product yield can reach 71.2%.
Above-mentioned example just for technical conceive of the present invention and technical characterstic are described, can not limit the scope of the invention with this.The equivalent transformation that all essence according to the present invention is done or modification, all should be encompassed within protection scope of the present invention.
Claims (4)
1. the preparation method of bis-benzal pentylcyclohexanone, is characterized in that, comprise the steps: to add a certain amount of 2 in the 250 mL there-necked flasks that agitator and reflux condensing tube be housed, 6-dimethylcyclohexanon, phenyl aldehyde and catalyzer, be heated to 180 ~ 230 DEG C of reaction 40 ~ 60min, filter, methanol aqueous solution is added in filtrate, put into ice bath cooling 20 ~ 30min simultaneously, by the crystal suction filtration of separating out, dry, obtain 2,6-bis-benzal pentylcyclohexanone.
2. the preparation method of 2,6-bis-benzal pentylcyclohexanone according to claim 1, is characterized in that, 2,6-described dimethylcyclohexanon and the mol ratio of phenyl aldehyde are: 1:2.0 ~ 3.0.
3. the preparation method of 2,6-bis-benzal pentylcyclohexanone according to claim 1, is characterized in that, described catalyzer is the vitriol oil and massfraction is the Pd/C of 10%.
4. the preparation method of 2,6-bis-benzal pentylcyclohexanone according to claim 3, is characterized in that, described methanol aqueous solution volume ratio is 1:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410748520.0A CN104529732A (en) | 2014-12-10 | 2014-12-10 | Preparation method for 2,6-dibenzylidenecyclohexanone |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410748520.0A CN104529732A (en) | 2014-12-10 | 2014-12-10 | Preparation method for 2,6-dibenzylidenecyclohexanone |
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| CN201410748520.0A Pending CN104529732A (en) | 2014-12-10 | 2014-12-10 | Preparation method for 2,6-dibenzylidenecyclohexanone |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106853374A (en) * | 2016-12-13 | 2017-06-16 | 徐州诺克非医药科技有限公司 | A kind of 2,6 2 benzal pentylcyclohexanone synthesis techniques as medicine and pesticide intermediate |
-
2014
- 2014-12-10 CN CN201410748520.0A patent/CN104529732A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106853374A (en) * | 2016-12-13 | 2017-06-16 | 徐州诺克非医药科技有限公司 | A kind of 2,6 2 benzal pentylcyclohexanone synthesis techniques as medicine and pesticide intermediate |
| CN106853374B (en) * | 2016-12-13 | 2019-04-30 | 甘肃泰升化工科技有限公司 | A kind of bis- benzal pentylcyclohexanone synthesis technology of 2,6- as medicine and pesticide intermediate |
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Application publication date: 20150422 |
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| WD01 | Invention patent application deemed withdrawn after publication |