AU2016102325A4 - Hexyl resorcinol drug intermediates 2-heptanone synthesis method - Google Patents
Hexyl resorcinol drug intermediates 2-heptanone synthesis method Download PDFInfo
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- AU2016102325A4 AU2016102325A4 AU2016102325A AU2016102325A AU2016102325A4 AU 2016102325 A4 AU2016102325 A4 AU 2016102325A4 AU 2016102325 A AU2016102325 A AU 2016102325A AU 2016102325 A AU2016102325 A AU 2016102325A AU 2016102325 A4 AU2016102325 A4 AU 2016102325A4
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- mass fraction
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- hexyl resorcinol
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Abstract
Hexyl resorcinol drug intermediates 2-heptanone synthesis method, comprising the following steps: equipped with a stirrer, a thermometer, a dropping funnel, the reaction vessel was added 2.1L potassium bisulfite solution, 1.6mol n-butyl-propionamide solution, 1.9-2.3mol 2-nitro-hypochlorous acid phenyl ester solution, 330ml nitroethane solution, stirring speed was controlled at 130-170rpm, the solution temperature was raised to 60-65 C,reacted for 7-9h, the oil layer was separated, adding sodium sulfite, the solution was adjusted to pH 9-10, the reaction was continued for 30-50min, reduce the temperature of the solution to10-15 C, the precipitated solid was washed with salt solution, washed with ethyl acetate solution, dehydrated with dehydrating agent, vacuum distillation, collecting fractions of 90-95 C, recrystallized from p-xylene solution, got crystals of 2-heptanone.
Description
Hexyl resorcinol drug intermediates 2-heptanone synthesis method
TECHNICAL FIELD
The present invention relates to hexyl resorcinol drug intermediates 2-heptanone synthesis method.
BACKGROUND ART
Hexyl resorcinol drug can inhibit the synthesis of ergosterol in the fungal cell membrane, the membrane structural was damaged, thereby inhibiting the growth of fungal cells. It acts on wool steroid C-14 demethylase, and wool steroid converting to C-14 demethylation wool steroids was inhibited, thus inhibiting the synthesis of ergosterol, it also has bacteriostatic and bactericidal effect on dermatophytes and yeasts. 2-heptanone as hexyl resorcinol drug intermediates, its synthesis method is of great economic significance for improving drug synthesis product quality, reducing the by-product content.
SUMMARY OF THE INVENTION
Object of the present invention is to provide hexyl resorcinol drug intermediates 2-heptanone synthesis method, comprising the following steps: (i) equipped with a stirrer, a thermometer, a dropping funnel, the reaction vessel was added 2.1L potassium bisulfite solution, 1.6mol n-butyl-propionamide solution, 1.9-2.3mol 2-nitro-hypochlorous acid phenyl ester solution, 330ml nitroethane solution, stirring speed was controlled at 130-170rpm, the solution temperature was raised to 60-65 °C,reacted for 7-9h, the oil layer was separated, adding sodium sulfite, the solution was adjusted to pH 9-10, the reaction was continued for 30-50min, reduce the temperature of the solution tol0-15°C, the precipitated solid was washed with salt solution, washed with ethyl acetate solution, dehydrated with dehydrating agent, vacuum distillation, collecting fractions of 90-95 °C, recrystallized from p-xylene solution, got crystals of 2-heptanone (1); wherein, the potassium bisulfite solution in step(i) has a mass fraction of 35-40%, the 2-nitro-hypochlorous acid phenyl ester solution in step(i) has a mass fraction of 65-70%, the sodium sulfite solution in step(i) has a mass fraction of 25-30%, the salt solution in step(i) is any one of ammonium bromide or sodium nitrate, the ethyl acetate solution in step(i) has a mass fraction of 75-80%, the dehydrating agent in step(i) is any one of phosphorus pentoxide or anhydrous calcium carbonate, the vacuum distillation in step(i) has a pressure of 1.7-1.9kPa, the p-xylene solution in step(i) has a mass fraction of 95-98%.
Throughout the reaction can be summarized as the following reaction formula:
Advantage of the present invention is that: reducing the reaction intermediate links, decreasing the reaction temperature and reaction time, improving the reaction yield.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS OF THE INVENTION
Embodiment 1
Equipped with a stirrer, a thermometer, a dropping funnel, the reaction vessel was added 2.1L potassium bisulfite solution with a mass fraction of 35%, 1.6mol n-butyl-propionamide solution, 1.9mol 2-nitro-hypochlorous acid phenyl ester solution with a mass fraction of 65%, 330ml nitroethane solution, stirring speed was controlled at 130rpm, the solution temperature was raised to 60 °C,reacted for 7h, the oil layer was separated, adding sodium sulfite solution with a mass fraction of 25%, the solution was adjusted to pH 9, the reaction was continued for 30min, reduce the temperature of the solution to 10°C, the precipitated solid was washed with ammonium bromide solution, washed with ethyl acetate solution with a mass fraction of 75%, dehydrated with phosphorus pentoxide, vacuum distillation at 1.7kPa, collecting fractions of 90-95 °C, recrystallized from p-xylene solution with a mass fraction of 95%, got crystals of 2-heptanone (1) 147.74g, yield 81%.
Embodiment 2
Equipped with a stirrer, a thermometer, a dropping funnel, the reaction vessel was added 2.1L potassium bisulfite solution with a mass fraction of 37%, 1.6mol n-butyl-propionamide solution, 2.1mol 2-nitro-hypochlorous acid phenyl ester solution with a mass fraction of 67%, 330ml nitroethane solution, stirring speed was controlled at 150rpm, the solution temperature was raised to 62 °C,reacted for 8h, the oil layer was separated, adding sodium sulfite solution with a mass fraction of 27%, the solution was adjusted to pH 9, the reaction was continued for 40min, reduce the temperature of the solution to 12°C, the precipitated solid was washed with sodium nitrate solution, washed with ethyl acetate solution with a mass fraction of 78%, dehydrated with anhydrous calcium carbonate, vacuum distillation at 1.8kPa, collecting fractions of 90-95 °C, recrystallized from p-xylene solution with a mass fraction of 97%, got crystals of 2-heptanone (1) 151.39g, yield 83%.
Embodiment 3
Equipped with a stirrer, a thermometer, a dropping funnel, the reaction vessel was added 2.1L potassium bisulfite solution with a mass fraction of 40%, 1.6mol n-butyl-propionamide solution, 2.3mol 2-nitro-hypochlorous acid phenyl ester solution with a mass fraction of 70%, 330ml nitroethane solution, stirring speed was controlled at 170rpm, the solution temperature was raised to 65 °C,reacted for 9h, the oil layer was separated, adding sodium sulfite solution with a mass fraction of 30%, the solution was adjusted to pH 10, the reaction was continued for 50min, reduce the temperature of the solution to 15°C, the precipitated solid was washed with ammonium bromide solution, washed with ethyl acetate solution with a mass fraction of 80%, dehydrated with phosphorus pentoxide, vacuum distillation at 1.9kPa, collecting fractions of 90-95 °C, recrystallized from p-xylene solution with a mass fraction of 98%, got crystals of 2-heptanone (1) 162.34g, yield 89%.
While a number of preferred embodiments have been described, it will be appreciated by persons skilled in the art that numerous variations and/or modifications may be made to the invention without departing from the spirit or scope of the invention as broadly described. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive.
Claims (4)
1. Hexyl resorcinol drug intermediates 2-heptanone synthesis method, comprising the following steps: (i) equipped with a stirrer, a thermometer, a dropping funnel, the reaction vessel was added 2.1L potassium bisulfite solution, 1.6mol n-butyl-propionamide solution, 1.9-2.3mol 2-nitro-hypochlorous acid phenyl ester solution, 330ml nitroethane solution, stirring speed was controlled at 130-170rpm, the solution temperature was raised to 60-65 °C,reacted for 7-9h, the oil layer was separated, adding sodium sulfite, the solution was adjusted to pH 9-10, the reaction was continued for 30-50min, reduce the temperature of the solution tol0-15°C, the precipitated solid was washed with salt solution, washed with ethyl acetate solution, dehydrated with dehydrating agent, vacuum distillation, collecting fractions of 90-95 °C, recrystallized from p-xylene solution, got crystals of 2-heptanone (1); wherein, the potassium bisulfite solution in step(i) has a mass fraction of 35-40%, the 2-nitro-hypochlorous acid phenyl ester solution in step(i) has a mass fraction of 65-70%, the sodium sulfite solution in step(i) has a mass fraction of 25-30%, the salt solution in step(i) is any one of ammonium bromide or sodium nitrate, the ethyl acetate solution in step(i) has a mass fraction of 75-80%.
2. Hexyl resorcinol drug intermediates 2-heptanone synthesis method according to claim 1 wherein the dehydrating agent in step(i) is any one of phosphorus pentoxide or anhydrous calcium carbonate.
3. Hexyl resorcinol drug intermediates 2-heptanone synthesis method according to claim 1 wherein the vacuum distillation in step(i) has a pressure of 1.7-1.9kPa.
4. Hexyl resorcinol drug intermediates 2-heptanone synthesis method according to claim 1 wherein the p-xylene solution in step(i) has a mass fraction of 95-98%.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510998994.5A CN105622373A (en) | 2015-12-25 | 2015-12-25 | Synthetic method for 4-hexyl-1,3-benzenediol drug intermediate 2-heptanone |
| CN2015109989945 | 2015-12-25 | ||
| CN2016108308537 | 2016-09-19 | ||
| CN201610830853.7A CN106431876A (en) | 2015-12-25 | 2016-09-19 | Hexylresorcinol drug intermediate 2-heptanone synthesis method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2016102325A4 true AU2016102325A4 (en) | 2017-02-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016102325A Ceased AU2016102325A4 (en) | 2015-12-25 | 2016-12-25 | Hexyl resorcinol drug intermediates 2-heptanone synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU2016102325A4 (en) |
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2016
- 2016-12-25 AU AU2016102325A patent/AU2016102325A4/en not_active Ceased
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| FGI | Letters patent sealed or granted (innovation patent) | ||
| MK22 | Patent ceased section 143a(d), or expired - non payment of renewal fee or expiry |