CN102875524A - Preparation method of 4'-formylbenzo 15-crown-5 - Google Patents
Preparation method of 4'-formylbenzo 15-crown-5 Download PDFInfo
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- CN102875524A CN102875524A CN2012104331729A CN201210433172A CN102875524A CN 102875524 A CN102875524 A CN 102875524A CN 2012104331729 A CN2012104331729 A CN 2012104331729A CN 201210433172 A CN201210433172 A CN 201210433172A CN 102875524 A CN102875524 A CN 102875524A
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Abstract
The invention provides a synthesis and purifying method of 4'-formylbenzo 15-crown-5. The method comprises the steps of weighing tetraethylene glycol dibenzensulfonate; dissolving in DMF (dimethyl formamide); adding 3, 4-dihydroxy benzaldehyde while agitating until completely being dissolved; and then slowly dropping sodium hydroxide; agitating to react at room temperature; then slowly heating; adding proper amount of water after the reaction, extracting through EA; concentrating organic phase to obtain brown oil substrate, and obtaining 2.6g of white solid which is 4'-formylbenzo 15-crown-5 through column chromatography. According to the method provided by the invention, the final product has the yield of more than 40%, the production method is scientific and reasonable; and detailed theoretical and practical guidelines are provided for follow-up expanding production.
Description
Technical field
The invention belongs to the compound preparation field, especially a kind of preparation method of 4 '-formyl benzo-15-crown-5.
Background technology
At present, because Bioexperiment makes new breakthroughs, make us in the process for the treatment of and the searching cause of disease, means are mistake more, the result is more accurate, so for treating various diseases the property pharmaceutical requirements is also increased gradually, therefore, various compounds with new function are in a large amount of being developed, and the whole world all has the new compound of the various difficult and complicated cases of opposing in searching, so in the process of these new compound exploitations, can produce the compound of numerous new textures and new configuration, and then searching is useful in these numerous new compounds, and the molecule for the treatment of use is arranged, and therefore developing new compound is one and important process.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, a kind of preparation method of 4 '-formyl benzo-15-crown-5 is provided, synthetic also this compound of purifying of the present invention makes its purity arrive certain requirement, can further test or application it.
The present invention realizes that the technical scheme of purpose is as follows:
A kind of preparation method of 4 '-formyl benzo-15-crown-5, step is as follows:
Take by weighing TEG DAADBSA ester, be dissolved in DMF, stir the lower 0412 that adds, fully after the dissolving, slowly be added dropwise to potassium hydroxide, slowly heat up after the stirring at room reaction, react complete rear adding suitable quantity of water, extract with EA, the concentrated brown oil that to get of organic phase gets white solid through column chromatography, get white solid 2.6g and be 4 '-the formyl benzo-15-crown-5;
And described TEG DAADBSA ester: the mass ratio of 0412 is 4:1-5.
Advantage of the present invention and beneficial effect are:
1, the invention provides a kind of synthetic and purification process of 4 '-formyl benzo-15-crown-5, its final product productive rate is 45.7%, and production method science, reasonable instructs for follow-up expanding production provides detailed theory and practice.
2, the invention provides synthesis condition, the raw material of each step in 4 '-formyl benzo-15-crown-5 building-up process, and the nuclear-magnetism figure of synthetic after product, for the analysis and identification of intermediate product in the building-up process provides detailed support.
Description of drawings
Fig. 1 be the present invention 4 '-the nuclear-magnetism figure of formyl benzo-15-crown-5,
1H NMR:1082019021 (300MHz, DMSO).
Embodiment
Below in conjunction with embodiment, technical scheme of the present invention is further specified, following embodiment is illustrative, is not determinate, can not limit protection scope of the present invention with following embodiment.
The preparation method's of the present invention 4 '-formyl benzo-15-crown-5 route map is as follows:
Raw material is as follows, is commercially available.
Sodium hydroxide
DMF
0412
Methylene dichloride
TEG DAADBSA ester
Sodium hydroxide
Sodium borohydride
Ammonium chloride
Methyl alcohol
1,7-pimeloyl chloride triethylamine
The preparation method of 4 '-formyl benzo-15-crown-5, step is as follows:
Take by weighing compound 1(4.3g), be dissolved in DMF, stir the lower 0412 (1.38g) that adds.After the dissolving, slowly be added dropwise to potassium hydroxide (1.68g) fully, slowly heat up after the stirring at room reaction.React complete rear adding suitable quantity of water, with the EA extraction, organic phase concentrates to get brown oil, gets white solid through column chromatography.Get white solid 2.6g and be compound 2, productive rate 45.7%.
Claims (2)
1. the preparation method of 4 '-formyl benzo-15-crown-5, it is characterized in that: step is as follows:
Take by weighing TEG DAADBSA ester, be dissolved in DMF, stir the lower 0412 that adds, fully after the dissolving, slowly be added dropwise to potassium hydroxide, slowly heat up after the stirring at room reaction, react complete rear adding suitable quantity of water, extract with EA, the concentrated brown oil that to get of organic phase gets white solid through column chromatography, get white solid 2.6g and be 4 '-the formyl benzo-15-crown-5.
2. the preparation method of 4 '-formyl benzo-15-crown-5 according to claim 1, it is characterized in that: described TEG DAADBSA ester: the mass ratio of 0412 is 4:1-5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN2012104331729A CN102875524A (en) | 2012-11-02 | 2012-11-02 | Preparation method of 4'-formylbenzo 15-crown-5 |
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| CN2012104331729A CN102875524A (en) | 2012-11-02 | 2012-11-02 | Preparation method of 4'-formylbenzo 15-crown-5 |
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| CN102875524A true CN102875524A (en) | 2013-01-16 |
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| CN2012104331729A Pending CN102875524A (en) | 2012-11-02 | 2012-11-02 | Preparation method of 4'-formylbenzo 15-crown-5 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111303050A (en) * | 2020-04-07 | 2020-06-19 | 西安近代化学研究所 | Synthesis method of bupirimate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101109708B (en) * | 2007-09-05 | 2010-05-19 | 南开大学 | Novel magnesium ion fluorescent probe and its manufacturing method and application |
-
2012
- 2012-11-02 CN CN2012104331729A patent/CN102875524A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101109708B (en) * | 2007-09-05 | 2010-05-19 | 南开大学 | Novel magnesium ion fluorescent probe and its manufacturing method and application |
Non-Patent Citations (1)
| Title |
|---|
| 杨山虎等: "超声波合成单苯并-12-冠-4", 《广州化工》, vol. 39, no. 18, 31 December 2011 (2011-12-31), pages 90 - 92 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111303050A (en) * | 2020-04-07 | 2020-06-19 | 西安近代化学研究所 | Synthesis method of bupirimate |
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Application publication date: 20130116 |