CN101712810A - Preparation method of laser dye 7-diethylamino-4-methylcoumarin - Google Patents
Preparation method of laser dye 7-diethylamino-4-methylcoumarin Download PDFInfo
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- CN101712810A CN101712810A CN 200810151992 CN200810151992A CN101712810A CN 101712810 A CN101712810 A CN 101712810A CN 200810151992 CN200810151992 CN 200810151992 CN 200810151992 A CN200810151992 A CN 200810151992A CN 101712810 A CN101712810 A CN 101712810A
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- methylcoumarin
- diethylin
- diethylamino
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Abstract
The invention belongs to a preparation method of laser dye 7-diethylamino-4-methylcoumarin, which comprises the following steps of: 1. mixing acetylacetic ether, m-diethylaminophenol, zinc chloride and stannous chloride for reaction; 2. washing a mixture after the reaction with acid, and drying to obtain a crude product of the 7-diethylamino-4-methylcoumarin; and 3. recrystallizing the crude product of the 7-diethylamino-4-methylcoumarin to obtain the 7-diethylamino-4-methylcoumarin satisfying laser use requirements. After conducting the technical processing of washing with acid and repeated recrystallization on the crude product of the laser dye 7-diethylamino-4-methylcoumarin, the impurities contained in the crude product of the laser dye 7-diethylamino-4-methylcoumarin can be effectively removed, the purity of the laser dye 7-diethylamino-4-methylcoumarin is effectively improved, the life of the laser dye 7-diethylamino-4-methylcoumarin in use is prolonged, and the economic performance for preparing the laser dye 7-diethylamino-4-methylcoumarin is markedly improved.
Description
Technical field
The invention belongs to the laser dyes field, the preparation method of especially a kind of laser dyes 7-diethylin-4-methylcoumarin.
Background technology
Along with developing rapidly of laser spectroscopy and laser chemistry, in the microcosmic course research work of separation of isotopes, directed synthetic chemistry reaction, need tunable dye lasers to be implemented on any wave band of near ultraviolet, visible light and infrared spectral region and carry out laser radiation.For obtaining high efficiency tunable laser and high-resolution laser spectrum, except that utilizing physical optics knowledge to improve the optical system, be a kind of letter and the easy method of row by means of the various laser dyess that can produce different laser spectrums.
7-diethylin-4-methylcoumarin laser dyes coumarin-1 that is otherwise known as, molecular formula is: C
14H
17NO
2, its structural formula is suc as formula (I), it be a kind of
Ideal laser dyes comparatively in the wave band has high-conversion rate, than the characteristics of wide tunable range.
The defective that the preparation method who is now adopted exists is: the purity of the laser dyes 7-diethylin-4-methylcoumarin of feasible preparation is lower, and the dyestuff life-span in use is shorter, and economy is relatively poor.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, provide a kind of and make that laser dyes 7-diethylin-4-methylcoumarin purity is higher, the preparation method of the laser dyes 7-diethylin-4-methylcoumarin of long service life and better economy.
The present invention solves its technical problem and is achieved through the following technical solutions:
The preparation method of a kind of laser dyes 7-diethylin-4-methylcoumarin is characterized in that: these preparation method's process following steps:
(1) methyl aceto acetate, m-diethylaminophenol, zinc chloride and tin protochloride are mixed, under 180 ℃ temperature condition, back flow reaction 2～5 hours is cooled to room temperature with reaction solution after reaction is finished;
(2) above-mentioned cooled reaction solution is mixed with dilute sulphuric acid, filtering reacting liquid is the acicular 7-diethylin of purple-4-methylcoumarin crude product behind the crystallizing and drying that leaches;
(3) with ethyl alcohol recrystallization 2～5 times of the thick product of 7-diethylin-4-methylcoumarin, the xln that leaches after to ethyl alcohol recrystallization with sherwood oil carries out recrystallization 2～5 times again, obtains the laser dyes 7-diethylin-4-methylcoumarin finished product of white needles after the filtration.
And methyl aceto acetate and m-diethylaminophenol weight ratio in the described step (1) are: 26/16.5, and milliliter/gram.
And the concentration of the dilute sulphuric acid in the described step (2) is 12%.
And the exsiccant temperature is in the described step (2): 30 ℃～50 ℃.
Advantage of the present invention and beneficial effect are:
The present invention is by carrying out pickling to laser dyes 7-diethylin-thick product of 4-methylcoumarin, repeatedly after the art breading of recrystallization, can remove the impurity that is contained in laser dyes 7-diethylin-thick product of 4-methylcoumarin effectively, improve the purity of laser dyes 7-diethylin-4-methylcoumarin effectively, prolong its life-span in use, significantly improve the economy of laser dyes 7-diethylin-4-methylcoumarin preparation.
Embodiment
The invention will be further described below by specific embodiment, and following examples are descriptive, is not determinate, can not limit protection scope of the present invention with this.
Embodiment 1:
(1) m-diethylaminophenol 16.5 gram (0.1 mol) and zinc chloride, tin protochloride (relation of the amount of the two and with the relation of the amount of other reactant) are mixed afterwards in the adding flask, the methyl aceto acetate reflux in oil bath that adds 26ml (0.2 mol) then, reacted 3.5 hours, and be cooled to room temperature;
(2) above-mentioned post reaction mixture being put into concentration is 12% dilute sulphuric acid, separates out purplish granular crystal body, leaches crystallized product, dry under 40 ℃, obtains 7-diethylin-4-methylcoumarin crude product;
(3) with ethyl alcohol recrystallization 2 times of the thick product of 7-diethylin-4-methylcoumarin, and then use the sherwood oil recrystallization again 2 times, promptly be met the laser dyes 7-diethylin-4-methylcoumarin of the white, needle-shaped crystals of laser service requirements.
Embodiment 2:
(1) m-diethylaminophenol 16.5 gram (0.1 mol) and zinc chloride, tin protochloride are mixed the back and add in the flask, add methyl aceto acetate reflux in oil bath of 26ml (0.2 mol) then, reacted 2 hours, be cooled to room temperature;
(2) above-mentioned post reaction mixture being put into concentration is 12% dilute sulphuric acid, separates out purplish granular crystal body, leaches crystallized product, dry under 30 ℃, obtains 7-diethylin-4-methylcoumarin crude product;
(3) with ethyl alcohol recrystallization 5 times of the thick product of 7-diethylin-4-methylcoumarin, and then use the sherwood oil recrystallization again 5 times, promptly be met the laser dyes 7-diethylin-4-methylcoumarin of the white, needle-shaped crystals of laser service requirements.
Embodiment 3:
(1) m-diethylaminophenol 16.5 gram (0.1 mol) and zinc chloride, tin protochloride are mixed the back and add in the flask, add methyl aceto acetate reflux in oil bath of 26ml (0.2 mol) then, reacted 5 hours, be cooled to room temperature;
(2) above-mentioned post reaction mixture being put into concentration is 12% dilute sulphuric acid, separates out purplish granular crystal body, leaches crystallized product, dry under 50 ℃, obtains 7-diethylin-4-methylcoumarin crude product;
(3) with the thick product of 7-diethylin-4-methylcoumarin with ethyl alcohol recrystallization 3 times, and then with sherwood oil recrystallization 3 times, promptly be met the laser dyes 7-diethylin-4-methylcoumarin of the white, needle-shaped crystals of laser service requirements.
Claims (4)
1. the preparation method of laser dyes 7-diethylin-4-methylcoumarin is characterized in that: this preparation method is through following steps:
(1) methyl aceto acetate, m-diethylaminophenol, zinc chloride and tin protochloride are mixed, under 180 ℃ temperature condition, back flow reaction 2～5 hours is cooled to room temperature with reaction solution after reaction is finished;
(2) above-mentioned cooled reaction solution is mixed with dilute sulphuric acid, filtering reacting liquid is the acicular 7-diethylin of purple-4-methylcoumarin crude product behind the crystallizing and drying that leaches;
(3) with ethyl alcohol recrystallization 2～5 times of the thick product of 7-diethylin-4-methylcoumarin, the xln that leaches after to ethyl alcohol recrystallization with sherwood oil carries out recrystallization 2～5 times again, obtains the laser dyes 7-diethylin-4-methylcoumarin finished product of white needles after the filtration.
2. the preparation method of laser dyes 7-diethylin according to claim 1-4-methylcoumarin is characterized in that: methyl aceto acetate and m-diethylaminophenol weight ratio in the described step (1) are: 26/16.5, and milliliter/gram.
3. the preparation method of laser dyes 7-diethylin according to claim 1-4-methylcoumarin is characterized in that: the concentration of the dilute sulphuric acid in the described step (2) is 12%.
4. the preparation method of laser dyes 7-diethylin according to claim 1-4-methylcoumarin is characterized in that: the exsiccant temperature is in the described step (2): 30 ℃～50 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200810151992 CN101712810A (en) | 2008-10-06 | 2008-10-06 | Preparation method of laser dye 7-diethylamino-4-methylcoumarin |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200810151992 CN101712810A (en) | 2008-10-06 | 2008-10-06 | Preparation method of laser dye 7-diethylamino-4-methylcoumarin |
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| CN101712810A true CN101712810A (en) | 2010-05-26 |
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| CN 200810151992 Pending CN101712810A (en) | 2008-10-06 | 2008-10-06 | Preparation method of laser dye 7-diethylamino-4-methylcoumarin |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103740360A (en) * | 2014-01-25 | 2014-04-23 | 厦门大学 | Fluorescent probe for detecting hypochlorous acid by fluorescence ratio method and preparation method for fluorescent probe |
| CN111548337A (en) * | 2020-06-08 | 2020-08-18 | 黄石市利福达医药化工有限公司 | Preparation method and application of 4-methyl-7-diethylamino coumarin |
-
2008
- 2008-10-06 CN CN 200810151992 patent/CN101712810A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103740360A (en) * | 2014-01-25 | 2014-04-23 | 厦门大学 | Fluorescent probe for detecting hypochlorous acid by fluorescence ratio method and preparation method for fluorescent probe |
| CN103740360B (en) * | 2014-01-25 | 2015-09-09 | 厦门大学 | Ratio fluorescent method detects hypochlorous fluorescent probe and preparation method thereof |
| CN111548337A (en) * | 2020-06-08 | 2020-08-18 | 黄石市利福达医药化工有限公司 | Preparation method and application of 4-methyl-7-diethylamino coumarin |
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Open date: 20100526 |