CN101486704A - Method for synthesizing muscolide - Google Patents
Method for synthesizing muscolide Download PDFInfo
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- CN101486704A CN101486704A CNA2009100961455A CN200910096145A CN101486704A CN 101486704 A CN101486704 A CN 101486704A CN A2009100961455 A CNA2009100961455 A CN A2009100961455A CN 200910096145 A CN200910096145 A CN 200910096145A CN 101486704 A CN101486704 A CN 101486704A
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Abstract
The invention relates to a synthetic method of muscolide, which adopts pentadecane dibasis acid synthesized by a biological fermentation method as a raw material and carries out an esterification reaction, a hydrolysis reaction and a reducing reaction to generate a product of 15-carbon hydroxy-acid. After a brominating reaction and a cyclization reaction, a muscolide product is finally obtained after purification. The synthetic method of the muscolide shortens synthetic route and reduces energy consumption, has simple technology, low cost, little pollution to environment, strong industrial operability and easy realization of industrialization.
Description
Technical field:
The present invention relates to a kind of synthetic method of thibetolide.
Background technology:
Thibetolide has another name called the Sunset Abelmoschus Root element
[7], molecular formula is C
15H
28O
2, molecular weight is 240.29, its skeleton symbol is as follows:
Thibetolide is a kind of important huge ring Moschus, natural being present in the angelica root oil, has strong, fine and smooth and graceful musky odor.It is again a good fixative in addition, can make essence keep fragrant breath enduringly, and this compound outward appearance is a white, needle-shaped crystals, fusing point 36-37 ℃, and 280 ℃ of boiling points.According to the data that RIFM provides, the acute toxicity data of thibetolide: oral LD
505g/Kg (rat), skin test LD
505g/Kg (rabbit).
Because thibetolide has good performance and high added value, attracted the various countries scientist to drop into huge financial resources and manpower is studied, present known synthetic method is concluded:
Synthetic method one
With α, ω-undecyne acid is raw material, with the butynol esterification, generates undecyne-(10)-acid-butine (4) ester, gets 15 carbon lactones through the cyclisation hydrogenation then.This side's processing condition maturation, yield is higher, has realized industrialization at present.
Synthetic method two
With 11-bromo undecanoic acid and hexanodioic acid is raw material, by 11-acetoxy group undecanoic acid, monoethyl adipatee, 15-acetoxy group pentadecylic acid ethyl ester, and 15-hydroxypentadecanoic acid, synthesize target compound 15 carbon lactones at last, this method processing condition maturation, yield is higher, has realized industrialization, but synthetic route is long, and investment is big.
Synthetic method three
Do raw material with Ethyl Hydrogen Azelate, electrolysis makes the Thapsic acid diethyl ester through the Kulbe synthesis method.Deducting a carbon atom with the Hunsdiecker method then is the bromo pentadecylic acid, reacts in alkalescence, gets 15-hydroxypentadecanoic acid, and then through polymerization, depolymerization gets product.This method processing condition maturation, yield is higher, is industrialized the earliest a kind of method.
Synthetic method four
With the undecylenic acid is raw material, and with the tetrahydrofuran (THF) reaction, esterification then, hydrolysis, cyclisation get 15 carbon lactones in the presence of superoxide.This method synthetic route is shorter, and raw material is easy to get, but processing condition are still immature, still locates the laboratory study stage now.
Synthetic method five
With 11-bromo undecanoic acid is raw material, carries out intermolecular elimination reaction with butynol, and hydrogenation then, cyclisation get 15 carbon lactones.This method synthetic route is shorter, and technology is simple, but processing condition are immature, fails to realize industrialization.
Synthetic method six
With undecyne acid is raw material, with the bromo butynol intermolecular elimination reaction takes place, and hydrogenation then, cyclisation get 15 carbon lactones.This method synthetic route is short, but raw material is difficult to obtain, and only rests on the laboratory study stage at present.
Synthetic method seven
With ten-olefin(e) acid methyl esters be raw material and acetate-5-hexene ester at WC16 with (Me) react in the presence of the 4Sn, hydrogenation then, hydrolysis, cyclisation get 15 carbon lactones.This method synthesis technique maturation, but acetate-5-hexene ester is difficult to obtain, and yield is on the low side, is difficult to industrialization.
Synthetic method eight
With 11-bromo undecanoic acid an alkali metal salt is sharp refined reagent react, hydrolysis under the low temperature then of raw material dative.Separate cyclisation and get 15 carbon lactones.This method synthetic route is short, and processing condition are than maturation but raw material valency height still is in the laboratory study stage at present.
Synthetic method nine
With 11-bromo undecanoic acid is raw material, at first makes the phenylsulfone of undecanoic acid, makes it the lactone ratio with tosic acid again after handling with 4-chloro-1-butanols, and removes the phenyl sulfuryl with sodium/amalgam or raney nickel and get 15 carbon lactones.This method processing condition maturation, raw material is easy to get, but yield is on the low side, is early stage laboratory study achievement.
Synthetic method ten
With the sinapinic acid is raw material, through ozonize, makes undecane dicarboxylic acid, reduce then 13 carbon glycol, under the HBr effect, make 13-bromine 13 carbon alcohol, allow itself and the effect of diethyl malonate sodium salt, hydrolysis decarboxylation makes the 15-hydroxypentadecanoic acid, and cyclisation gets 15 carbon lactones.This method raw material is easy to get, but the long investment of operational path is big, only is in the laboratory study stage at present.
Synthetic method 11
A kind of oilseed plant with China southwest---malania oleifera oil, tetracosa carbon-15-the olefin(e) acid that obtains through saponification is a raw material, make 15-hydroxypentadecanoic acid by ozonize one reduction reaction, then through polycondensation, depolymerization promptly get 15 carbon lactones, this method operational path is shorter, yield is higher, but raw material sources are limited, are difficult to industrialization.
Synthetic method 12
With 12 carbon glycol, methyl acrylate is raw material, and perhydronaphthalene is a solvent, makes 11-hydroxyl-11 alkyl-gamma-butyrolactone under the catalysis of peroxidation uncle butyl ether, and shortening gets the 15-hydroxypentadecanoic acid then, and cyclisation gets 15 carbon lactones.This method operational path is shorter, but yield is on the low side, still stays in the laboratory study stage at present.
Synthetic method 13
With the pimelinketone is raw material, under acidic conditions, make 1 with hydroperoxidation, 1-diperoxy hydrogen base dicyclohexyl superoxide, react with cyclopentanone again, then thermal degradation gets 15 carbon lactones and big ring hydrocarbon polymer in decane. and this method operational path is short, raw material is easy to get, but processing condition are immature, yield is low, are difficult to industrialization.
More than these known synthetic technology routes its weak point is all respectively arranged, the raw material that has is not easy to obtain, price is expensive, cost is high; The reactions steps that has is many, technical process is long, the working condition harshness, and investment is high, yield is low, cost is high.
Summary of the invention:
The object of the present invention is to provide a kind of synthetic method of thibetolide.The object of the present invention is achieved like this, and the synthetic method of this thibetolide may further comprise the steps:
(1) generates 15 carbon, two dibutyl phthalates by the reaction of 15 carbon dicarboxylic acids;
(2) by the synthetic 15 carbon list acid monoester salt of resulting 15 carbon of step (1) two dibutyl phthalates;
(3) with the resulting 15 carbon list acid monoester salt of step (2) through acidifying, handle to obtain 15 carbon list acid monoesters;
(4) the 15 carbon list acid monoesters that step (3) obtained generate 15 carbon hydroxy esters by reduction reaction;
(5) the resulting 15 carbon hydroxy esters of step (4) are generated 15 carbon alcohol acids by hydrolysis reaction;
(6) the 15 carbon alcohol acid solids that step (5) obtained obtain 15 carbon alcohol acid bromination products by bromo-reaction;
(7) get quantitative 15 carbon alcohol acid bromination products and be dissolved in the organic solvent, ring closure reaction obtains the thibetolide crude product;
(8) purification of thibetolide crude product is obtained the thibetolide product.
Further introduce the present invention, above-mentioned steps (1)-(8) are specially:
(1) 15 carbon dicarboxylic acids are mixed with organic alcoholic solution, this organic alcohol can be propyl carbinol, methyl alcohol.Add little amount of catalyst and an amount of band aqua under 80-120 ℃ of agitation conditions, this catalyzer is a solid acid, as NaHSO
4Deng, this band aqua is a hexanaphthene, the reaction times is 2-8 hours.Filter, be washed to neutrality, organic solvent is removed in distillation then, obtains 15 carbon, two dibutyl phthalates;
(2) quantitative oxyhydroxide is dissolved in the organic solvent, this oxyhydroxide is hydrated barta, calcium hydroxide, potassium hydroxide, and lithium hydroxide.Organic solvent is methyl alcohol, ethanol.Under 0-50 ℃ of agitation condition, slowly be added drop-wise in resulting 15 carbon of step (1) two dibutyl phthalates, filter, wash, synthetic 15 carbon list acid monoester salt.Reaction times is 2-12 hours;
(3) be acid with acid solution with the aqueous solution furnishing PH of the resulting 15 carbon list acid monoester salt of step (2), this acid solution is a hydrochloric acid soln, sulphuric acid soln.Use the organic solvent extraction aqueous phase solution then repeatedly, merge organic phase, be washed to neutrality, and dry.After steaming desolventizes, the 15 carbon list acid monoesters that obtain;
(4) at ambient temperature, the 15 carbon list acid monoesters that step (3) is obtained mix with hydroborate and iodine, are dissolved in the organic solvent, at room temperature react 1-6 hours.Steaming desolventizes, and uses organic solvent extraction again, is washed till neutrality, and dry back is steamed and desolventized, and obtains 15 carbon hydroxy esters.This hydroborate is the boron sodium cyanide, and this organic solvent can be an ethyl acetate, also can be the second eyeball, acetone, tetrahydrofuran (THF) or sherwood oil;
(5) the resulting 15 carbon hydroxy esters of step (4) are mixed with quantitative oxyhydroxide, be dissolved in organic solvent, under 0-100 ℃ condition, reacted 2-10 hours.This oxyhydroxide is sodium hydroxide, calcium hydroxide, potassium hydroxide, and lithium hydroxide.Steaming desolventizes Hou Jiashui, and to be acidified to pH value be 2.Suction filtration obtains 15 carbon alcohol acids;
(6) the 15 carbon alcohol acid solids that step (5) obtained are dissolved in the mixed solution of Hydrogen bromide and Glacial acetic acid, and in anaerobic, reaction is 10-36 hour under 50-150 ℃ the condition, obtains 15 carbon alcohol acid bromination products;
(7) get quantitative 15 carbon alcohol acid bromination products and be dissolved in the organic solvent, this organic solvent can be ethyl acetate, also can be toluene, dimethylbenzene or dimethyl sulfoxide (DMSO).Anhydrous, add carbonate under 20-100 ℃ of conditions, this carbonate can be Quilonum Retard, yellow soda ash, salt of wormwood, reaction 1-10 hour is steamed and is removed organic solvent, obtains the thibetolide crude product;
(8) the thibetolide crude product is carried out underpressure distillation, collect the cut of 130-140 ℃/2mmHg, obtain the thibetolide product, by detecting, encircling 15 content with lactone is 90%.Reaction yield is 50%-60%.
This method technology is simple, and energy consumption is low, and cost is low, and environmental pollution is little, and industry is workable, is easy to realize industrialization.
Embodiment:
Further illustrate content of the present invention below in conjunction with example.
Embodiment 1
15 carbon dicarboxylic acid 27.2g are mixed with the 64ml propyl carbinol, add 4g sodium pyrosulfate and 10ml hexanaphthene under 115 ℃ of agitation conditions, the reaction times is 4 hours.Filter, be washed to neutrality, organic solvent is removed in distillation then, obtains 34.7g 15 carbon two dibutyl phthalates.The 25g hydrated barta is dissolved in the methyl alcohol, at room temperature, slowly is added drop-wise in 30g 15 carbon two dibutyl phthalates, reacted 14 hours, filter, wash, synthetic 15 carbon list acid monoester salt.After adding the less water dilution, be 2 with dilute hydrochloric acid with solution furnishing PH, and use ethyl acetate extraction, be washed to neutrality, steam, obtain 21.2g 15 carbon list acid monoester solids except that behind the organic solvent.
Under 0 ℃ of condition, take by weighing 10g 15 carbon list acid monoesters and mix with 3.3g hydroborate and 8.9 iodine, be dissolved in the 200ml tetrahydrofuran solution, at room temperature reacted 3 hours.Steaming desolventizes, and uses ethyl acetate extraction again, is washed till neutrality, after dry steaming desolventizes, obtains 15 carbon hydroxy ester 8.2g.It is dissolved in the 100ml tetrahydrofuran (THF), add the 3.4g lithium hydroxide, at room temperature reacted 2 hours, steaming desolventizes the back and drips suction hydrochloric acid furnishing acidity, filters and obtains 7g 15 carbon alcohol acids.
7g 15 carbon alcohol acids are dissolved in 200ml Hydrogen bromide and the 300ml Glacial acetic acid mixed solution, and in anaerobic, reflux conditions reacted 10 hours down, obtained the 15 carbon alcohol acid bromination products of 8g.Get 5g 15 carbon alcohol acid bromination products again and be dissolved in the 500ml dimethylsulfoxide solvent, and add the 5g potassium carbonate powder, under 150 ℃ of conditions, reacted 6 hours, steam and remove most of organic solvent, obtain the thibetolide crude product.
The thibetolide crude product is carried out underpressure distillation, collect the cut of 130-140 ℃/2mmHg, obtain thibetolide product 3.2g, by detecting, encircling 15 content with lactone is 90%.
Embodiment 2
15 carbon dicarboxylic acid 27.2g are mixed with the 50ml propyl carbinol, add 4g sodium pyrosulfate and 10ml hexanaphthene under 110 ℃ of agitation conditions, the reaction times is 6 hours.Filter, be washed to neutrality, organic solvent is removed in distillation then, obtains 34.7g 15 carbon two dibutyl phthalates.The 18g hydrated barta is dissolved in the mixing solutions of first alcohol and water, at room temperature, slowly is added drop-wise in 30g 15 carbon two dibutyl phthalates, reacted 24 hours, filter, wash, synthetic 15 carbon list acid monoester salt.After adding the less water dilution, be 2 with solution furnishing PH, and, be washed to neutrality that steam except that behind the organic solvent, 20.8g obtains 15 carbon list acid monoester solids of white with the toluene extraction with dilute hydrochloric acid.
Under 0 ℃ of condition, take by weighing 10g 15 carbon list acid monoesters and mix with 3.3g hydroborate and 8.9 iodine, be dissolved in the 200ml tetrahydrofuran solution, at room temperature reacted 3 hours.Steaming desolventizes, and with the toluene extraction, is washed till neutrality again, after dry steaming desolventizes, obtains 15 carbon hydroxy ester 7.8g.It is dissolved in the 100ml tetrahydrofuran (THF), add the 3.2g lithium hydroxide, at room temperature reacted 5 hours, steaming desolventizes the back and drips suction hydrochloric acid furnishing acidity, filters and obtains 6.4g 15 carbon alcohol acids.
6.4g 15 carbon alcohol acids are dissolved in 400ml Hydrogen bromide and the 500ml Glacial acetic acid mixed solution, and in anaerobic, reflux conditions reacted 5 hours down, obtained the 15 carbon alcohol acid bromination products of 6g.Get 5g 15 carbon alcohol acid bromination products again and be dissolved in the 250ml dimethylsulfoxide solvent, and add the 5g powdered sodium carbonate, under 80 ℃ of conditions, reacted 10 hours, steam and remove most of organic solvent, obtain the thibetolide crude product.
The thibetolide crude product is carried out underpressure distillation, collect the cut of 130-140 ℃/2mmHg, obtain thibetolide product 2.8g, by detecting, encircling 15 content with lactone is 88%.
Embodiment 3
15 carbon dicarboxylic acid 105g are mixed with the 400ml propyl carbinol, add 20g sodium pyrosulfate and 20ml hexanaphthene under 110 ℃ of agitation conditions, the reaction times is 6 hours.Filter, be washed to neutrality, organic solvent is removed in distillation then, obtains 142g 15 carbon two dibutyl phthalates.The 100g hydrated barta is dissolved in the mixing solutions of first alcohol and water, at room temperature, slowly is added drop-wise in 130g 15 carbon two dibutyl phthalates, reacted 12 hours, filter, wash, synthetic 15 carbon list acid monoester salt.After adding the less water dilution, be 2 with solution furnishing PH, and, be washed to neutrality that steam except that behind the organic solvent, 87.5g obtains 15 carbon list acid monoester solids of white with the toluene extraction with dilute hydrochloric acid.
Under 10 ℃ of conditions, take by weighing 50g 15 carbon list acid monoesters and mix with 16.6g hydroborate and 44.5 iodine, be dissolved in the 400ml tetrahydrofuran solution, at room temperature reacted 3 hours.Steaming desolventizes, and with the toluene extraction, is washed till neutrality again, after dry steaming desolventizes, obtains 15 carbon hydroxy ester 45g.It is dissolved in the 200ml tetrahydrofuran (THF), add the 10.5g lithium hydroxide, at room temperature reacted 5 hours, steaming desolventizes the back and drips suction hydrochloric acid furnishing acidity, filters and obtains 40.3g 15 carbon alcohol acids.
40g 15 carbon alcohol acids are dissolved in 1000ml Hydrogen bromide and the 1000ml Glacial acetic acid mixed solution, and in anaerobic, reflux conditions reacted 15 hours down, obtained the 15 carbon alcohol acid bromination products of 46g.Get 30g 15 carbon alcohol acid bromination products again and be dissolved in the 3000ml dimethylsulfoxide solvent, and add 30g Quilonum Retard powder, under 120 ℃ of conditions, reacted 8 hours, steam and remove most of organic solvent, obtain the thibetolide crude product.
The thibetolide crude product is carried out underpressure distillation, collect the cut of 130-140 ℃/2mmHg, obtain thibetolide product 18.1g, by detecting, encircling 15 content with lactone is 89%.
Claims (15)
1. the synthetic method of a thibetolide is characterized in that this method may further comprise the steps:
(1) generates 15 carbon, two dibutyl phthalates by the reaction of 15 carbon dicarboxylic acids;
(2) by the synthetic 15 carbon list acid monoester salt of resulting 15 carbon of step (1) two dibutyl phthalates;
(3) with the resulting 15 carbon list acid monoester salt of step (2) through acidification, obtain 15 carbon list acid monoesters;
(4) the 15 carbon list acid monoesters that step (3) obtained generate 15 carbon hydroxy esters by reduction reaction;
(5) the resulting 15 carbon hydroxy esters of step (4) are generated 15 carbon alcohol acids by hydrolysis reaction;
(6) the 15 carbon alcohol acids that step (5) is obtained generate 15 carbon alcohol acid bromination products by bromo-reaction;
(7) get quantitative 15 carbon alcohol acid bromination products and be dissolved in the organic solvent, add quantitative carbonate powder, after the reaction, steam and remove organic solvent, obtain the thibetolide crude product;
(8) purification of thibetolide crude product is obtained the thibetolide product.
2. the synthetic method of thibetolide according to claim 1 is characterized in that:
Wherein step (1) is that 15 carbon dicarboxylic acids are mixed with organic alcoholic solution, and reaction obtains 15 carbon, two dibutyl phthalates;
Wherein step (2) is added drop-wise in resulting 15 carbon of step (1) two dibutyl phthalates for quantitative oxyhydroxide is dissolved in the organic solvent, obtains 15 carbon list acid monoester salt;
Wherein step (3) be with acid solution with the aqueous solution furnishing PH of the resulting 15 carbon list acid monoester salt of step (2) for acid, use the organic solvent extraction aqueous phase solution then, merge organic phase, washing is also dry, obtains 15 carbon list acid monoesters;
Wherein step (4) is mixed with hydroborate and iodine for 15 carbon list acid monoesters that step (3) is obtained, is dissolved in the organic solvent instead, and steaming desolventizes, extract, and drying, steaming desolventizes, and obtains 15 carbon hydroxy esters;
Wherein step (5) is that the resulting 15 carbon hydroxy esters of step (4) are mixed with quantitative oxyhydroxide, is dissolved in the organic solvent reaction, adds the water acidifying after steaming desolventizes, and obtains 15 carbon alcohol acids.
Wherein step (6) is reacted for the mixing solutions that the 15 carbon alcohol acids that step (5) is obtained are dissolved in Hydrogen bromide and Glacial acetic acid;
Wherein step (7) is dissolved in the organic solvent and reacts for getting quantitative 15 carbon alcohol acid bromination products, steams and removes organic solvent, obtains the thibetolide crude product;
Wherein step (8) is collected cut for the thibetolide crude product is carried out underpressure distillation, obtains the thibetolide product.
3. according to the synthetic method of claim 2 kind of described thibetolide, it is characterized in that:
Wherein step (1) is that 15 carbon dicarboxylic acids are mixed with organic alcoholic solution, adds little amount of catalyst and an amount of band aqua under 80-120 ℃ of agitation conditions, and the reaction times is 2-8 hours, obtains 15 carbon, two dibutyl phthalates;
Wherein step (2) is for to be dissolved in quantitative oxyhydroxide in the organic solvent, under 0-50 ℃ of agitation condition, slowly be added drop-wise in resulting 15 carbon of step (1) two dibutyl phthalates, filter, wash, the aqueous solution of synthetic 15 carbon list acid monoester salt, the reaction times is 2-12 hours;
Wherein step (3) is for being 1-6 with acid solution with the aqueous solution furnishing PH of the resulting 15 carbon list acid monoester salt of step (2), use the organic solvent extraction aqueous phase solution then repeatedly, merge organic phase, washing is also dry, after steaming desolventizes, obtain 15 carbon list acid monoesters;
Wherein step (4) is under 0-50 ℃ of condition, and the 15 carbon list acid monoesters that step (3) is obtained mix with hydroborate and iodine, are dissolved in the organic solvent, at room temperature reacted 1-6 hours, steaming desolventizes, and uses organic solvent extraction again, steaming desolventizes after the water drying, obtains 15 carbon hydroxy esters;
Wherein step (5) is that the resulting 15 carbon hydroxy esters of step (4) are mixed with quantitative oxyhydroxide, be dissolved in organic solvent, under 0-100 ℃ condition, reacted 2-10 hours, steam and to desolventize Hou Jiashui to be acidified to pH value be 1-5, suction filtration obtains 15 carbon alcohol acids;
Wherein step (6) is for the mixing solutions that is dissolved in Hydrogen bromide and Glacial acetic acid of 15 carbon alcohol acids that step (5) is obtained, in anaerobic, and reflux conditions reaction 10-48 hour down;
Wherein step (7) is dissolved in the organic solvent and reacts for getting quantitative 15 carbon alcohol acid bromination products, adds quantitative carbonate powder, and under 50-120 ℃ condition, reaction 2-10 hour is steamed and removed organic solvent, obtains the thibetolide crude product;
Wherein step (8) is collected the cut of 130-140 ℃/2mmHg for the thibetolide crude product is carried out underpressure distillation, obtains the thibetolide product.
4. according to the synthetic method of claim 3 kind of described thibetolide, it is characterized in that:
Wherein step (5) is that the resulting 15 carbon hydroxy esters of step (4) are mixed with quantitative oxyhydroxide, be dissolved in organic solvent, under 0-50 ℃ condition, reacted 2-10 hours, steam and to desolventize Hou Jiashui to be acidified to pH value be 2, suction filtration obtains 15 carbon alcohol acids.
5. according to the synthetic method of claim 3 kind of described thibetolide, it is characterized in that: the organic solvent mentioned in steps be ethyl acetate, toluene, dimethylbenzene, tetrahydrofuran (THF), sherwood oil, second eyeball, acetone or tetrahydrofuran (THF).
6. according to the synthetic method of claim 3 kind of described thibetolide, it is characterized in that: the described organic alcohol of step (1) is propyl carbinol, methyl alcohol, and consumption is 5-10 a times of pentadecane diacid.
7. according to the synthetic method of claim 3 kind of described thibetolide, it is characterized in that: the catalyzer in the step (1) is a solid acid catalyst.
8. according to the synthetic method of claim 3 kind of described thibetolide, it is characterized in that: the band aqua in the step (1) is hexanaphthene, toluene.
9. according to the synthetic method of claim a kind of described thibetolide, it is characterized in that: the oxyhydroxide in the step (2) is sodium hydroxide, calcium hydroxide, hydrated barta, and its consumption is 1-2 a times of 15 carbon, two dibutyl phthalates.
10. according to the synthetic method of claim 3 kind of described thibetolide, it is characterized in that: the organic solvent in the step (2) is methyl alcohol, ethanol.
11. the synthetic method according to claim 3 kind of described thibetolide is characterized in that: the hydroborate in the step (4) is a sodium borohydride.
12. the synthetic method according to claim 3 kind of described thibetolide is characterized in that: the raw material consumption 15 carbon list acid monoesters in the step (4): hydroborate: iodine is 1: 2.5-5: 1.
13. the synthetic method according to claim 3 kind of described thibetolide is characterized in that: the oxyhydroxide in the step (5) is lithium hydroxide, potassium hydroxide, and its consumption is 1-5 a times of 15 carbon hydroxy esters.
14. synthetic method according to claim 3 kind of described thibetolide, it is characterized in that: the consumption 15 carbon alcohol acid bromination products of the raw material in the step (7): carbonate is 1:2, and organic solvent is ethyl acetate, toluene, dimethylbenzene or dimethyl sulfoxide (DMSO).
15. the synthetic method according to claim 3 kind of described thibetolide is characterized in that: the carbonate powder in the step (7) is yellow soda ash, salt of wormwood.
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| CNA2009100961455A CN101486704A (en) | 2009-02-16 | 2009-02-16 | Method for synthesizing muscolide |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102816142A (en) * | 2012-08-22 | 2012-12-12 | 福建天富生物科技发展有限公司 | Synthesis method for pentadecanoicacid |
| CN107365290A (en) * | 2017-08-10 | 2017-11-21 | 王显权 | The method that Malania Oleifera Oil prepares pentadacanolide |
| CN108383723A (en) * | 2018-03-23 | 2018-08-10 | 淄博职业学院 | The preparation method of high-purity, high yield Beta-methyl monomethyl glutarate |
-
2009
- 2009-02-16 CN CNA2009100961455A patent/CN101486704A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102816142A (en) * | 2012-08-22 | 2012-12-12 | 福建天富生物科技发展有限公司 | Synthesis method for pentadecanoicacid |
| CN107365290A (en) * | 2017-08-10 | 2017-11-21 | 王显权 | The method that Malania Oleifera Oil prepares pentadacanolide |
| CN108383723A (en) * | 2018-03-23 | 2018-08-10 | 淄博职业学院 | The preparation method of high-purity, high yield Beta-methyl monomethyl glutarate |
| CN108383723B (en) * | 2018-03-23 | 2021-03-23 | 淄博职业学院 | Preparation method of beta-methyl glutarate monomethyl ester with high purity and high yield |
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