AU2018100829A4 - Organic synthesis intermediates 2-octanal aldehyde synthesis method - Google Patents
Organic synthesis intermediates 2-octanal aldehyde synthesis method Download PDFInfo
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- AU2018100829A4 AU2018100829A4 AU2018100829A AU2018100829A AU2018100829A4 AU 2018100829 A4 AU2018100829 A4 AU 2018100829A4 AU 2018100829 A AU2018100829 A AU 2018100829A AU 2018100829 A AU2018100829 A AU 2018100829A AU 2018100829 A4 AU2018100829 A4 AU 2018100829A4
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- 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
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Abstract
Organic synthesis intermediates 2-octanal aldehyde synthesis method Abstract 5 The present invention discloses organic synthesis intermediates 2-octanal aldehyde synthesis method, comprises the following steps:2-octyne- 1 -propan-ether and anhydrous 2-bromopropane solution were added to the reaction vessel, controlled the temperature of the solution, controlled the stirring speed, reacted; and then added cadmium selenate powder in batches and anhydrous ethylene glycol carbonate 10 solution, raised the temperature, continued to react, reduced the temperature, standing still, the solution was layered, separated from the oil layer, washed in anhydrous 2,5-dimethylfuran solution for several times, washed in anhydrous dimethyl sulfoxide solution for several times, recrystallized in anhydrous diethylene glycol solution, dehydrated with dehydration, got the finished product 2-octenal aldehyde.
Description
The present invention discloses organic synthesis intermediates 2-octanal aldehyde synthesis method, comprises the following steps:2-octyne-l-propan-ether and anhydrous 2-bromopropane solution were added to the reaction vessel, controlled the temperature of the solution, controlled the stirring speed, reacted; and then added cadmium selenate powder in batches and anhydrous ethylene glycol carbonate solution, raised the temperature, continued to react, reduced the temperature, standing still, the solution was layered, separated from the oil layer, washed in anhydrous
2,5-dimethylfuran solution for several times, washed in anhydrous dimethyl sulfoxide solution for several times, recrystallized in anhydrous diethylene glycol solution, dehydrated with dehydration, got the finished product 2-octenal aldehyde.
2018100829 19 Jun 2018
Organic synthesis intermediates 2-octanal aldehyde synthesis method
FIELD OF THE INVENTION
The present invention relates to a method for preparing a pharmaceutical 5 intermediate which belongs to the field of organic synthesis, more particularly, relates to organic synthesis intermediates 2-octanal aldehyde synthesis method.
GENERAL BACKGROUND
2-octynal aldehyde is mainly used as organic synthesis intermediates, the existing synthesis method is mostly use chromate pyridine hydrochloride as reactants, generates the 2-octenoaldehyde. This method of production requires chromate compound as raw materials, which will lead to pollutant handling procedures are more complex, increases the cost of treatment; the presence of hydrochloride requires a higher anti-corrosion treatment on equipment, resulting in higher production costs, it is not conducive to control the cost, and the synthesis method is complicated. Therefore, it is necessary to propose a new synthesis method.
SUMMARY
Based on the technical problems of the background technology, the purpose of the present invention is to provide organic synthesis intermediates 2-octanal aldehyde synthesis method, comprises the following steps:
A: 2-octyne-l-propan-ether and 900 ml anhydrous 2-bromopropane solution were added to the reaction vessel, controlled the temperature of the solution at 30-37°C, controlled the stirring speed at 180-210 rpm, reacted for 80-110 min;
B: and then added cadmium selenate powder in 40 min in batches and anhydrous ethylene glycol carbonate solution, raised the temperature to 40-46 °C, continued to react for 2-3 h, reduced the temperature to 10-15 °C, standing still for 90-130 min, the solution was layered, separated from the oil layer, washed in anhydrous
2,5-dimethylfuran solution for several times, washed in anhydrous dimethyl sulfoxide solution for several times, recrystallized in anhydrous diethylene glycol solution,
2018100829 19 Jun 2018 dehydrated with dehydration, got the finished product 2-octenal aldehyde.
Preferably, the dehydrating agent is any one of anhydrous magnesium sulfate and anhydrous calcium sulfate.
Throughout the reaction process can be the following reaction formula:
CH3(CH2hC^HCCH2OCH2CH2CH3 + CdSe + C3H4O5 -► CH3(CH2)4C=CCHO
Compared with the synthesis method disclosed in the background art, the invention provides organic synthesis intermediates 2-octanal aldehyde synthesis method, it is unnecessary to use chromate compound as raw materials, which avoids the complicated process of pollutant treatment and reduces the cost of treatment. In addition, it avoids the corrosion of the hydrochloride to the reaction equipment, reduces the anti-corrosion treatment requirements, reduces the production cost, which is advantageous to the cost control and the economic production, reduces intermediate links reaction, decreases the reaction time and improves the reaction yield, at the same time, the present invention provides a new synthetic route which has laid a good foundation for further enhancing the yield of the reaction.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples with reference to specific embodiments of the present invention are further illustrated:
Embodiment 1
Organic synthesis intermediates 2-octanal aldehyde synthesis method, comprises the following steps:
A: 2mol 2-octyne-l-propan-ether and 900 ml anhydrous 2-bromopropane solution were added to the reaction vessel, controlled the temperature of the solution at 30°C, controlled the stirring speed at 180 rpm, reacted for 80 min;
B: and then added 2 mol cadmium selenate powder in 40 min in 3 times and 4 mol anhydrous ethylene glycol carbonate solution, raised the temperature to 40 °C , continued to react for 2 h, reduced the temperature to 10 °C, standing still for 90 min, the solution was layered, separated from the oil layer, washed in anhydrous
2018100829 19 Jun 2018
2,5-dimethylfuran solution for 2 times, washed in anhydrous dimethyl sulfoxide solution for 4 times, recrystallized in anhydrous diethylene glycol solution, dehydrated with anhydrous magnesium sulfate dehydration, got the finished product 2-octenal aldehyde 218.4g, yield of 88%.
Embodiment 2
Organic synthesis intermediates 2-octanal aldehyde synthesis method, comprises the following steps:
A: 2mol 2-octyne-l-propan-ether and 900 ml anhydrous 2-bromopropane solution 10 were added to the reaction vessel, controlled the temperature of the solution at 35 °C, controlled the stirring speed at 190 rpm, reacted for 100 min;
B: and then added 2.5 mol cadmium selenate powder in 40 min in 4 times and 4.5 mol anhydrous ethylene glycol carbonate solution, raised the temperature to 44 °C, continued to react for 2.5 h, reduced the temperature to 13 °C, standing still for 110 min, the solution was layered, separated from the oil layer, washed in anhydrous
2,5-dimethylfuran solution for 3 times, washed in anhydrous dimethyl sulfoxide solution for 5 times, recrystallized in anhydrous diethylene glycol solution, dehydrated with anhydrous calcium sulfate dehydration, got the finished product 2-octenal aldehyde 228.16g, yield of 92%.
Embodiment 3
Organic synthesis intermediates 2-octanal aldehyde synthesis method, comprises the following steps:
A: 2mol 2-octyne-l-propan-ether and 900 ml anhydrous 2-bromopropane solution were added to the reaction vessel, controlled the temperature of the solution at 37°C, controlled the stirring speed at 210 rpm, reacted for 110 min;
B: and then added 3 mol cadmium selenate powder in 40 min in 5 times and 5 mol anhydrous ethylene glycol carbonate solution, raised the temperature to 46 °C , continued to react for 3 h, reduced the temperature to 15 °C, standing still for 130 min, the solution was layered, separated from the oil layer, washed in anhydrous
2018100829 19 Jun 2018
2,5-dimethylfuran solution for 4 times, washed in anhydrous dimethyl sulfoxide solution for 6 times, recrystallized in anhydrous diethylene glycol solution, dehydrated with anhydrous magnesium sulfate dehydration, got the finished product 2-octenal aldehyde 223.6g, yield of 95%.
The embodiments of the present invention are merely preferred embodiments of the present invention, but the range of the present invention is not limited this, and any person who is familiar with those skilled in the arts, within the technical range of the present invention. It is intended that the technical solution and its inventive concept be replaced or modified equivalently with reference to the range of the invention.
2018100829 19 Jun 2018
Claims (2)
- Claims1. Organic synthesis intermediates 2-octanal aldehyde synthesis method, comprises the following steps:5 A: 2-octyne-l-propan-ether and 900 ml anhydrous 2-bromopropane solution were added to the reaction vessel, controlled the temperature of the solution at 30-37°C, controlled the stirring speed at 180-210 rpm, reacted for 80-110 min;B: and then added cadmium selenate powder in 40 min in batches and anhydrous ethylene glycol carbonate solution, raised the temperature to 40-46 °C, continued to10 react for 2-3 h, reduced the temperature to 10-15 °C, standing still for 90-130 min, the solution was layered, separated from the oil layer, washed in anhydrous
- 2,5-dimethylfuran solution for several times, washed in anhydrous dimethyl sulfoxide solution for several times, recrystallized in anhydrous diethylene glycol solution, dehydrated with dehydration, got the finished product 2-octenal aldehyde.2. Organic synthesis intermediates 2-octanal aldehyde synthesis method according to claim 1 wherein the dehydrating agent is any one of anhydrous magnesium sulfate and anhydrous calcium sulfate.20 3. Organic synthesis intermediates 2-octanal aldehyde synthesis method according to claim 1 wherein, comprises the following steps:A: 3mol 4-nitro-6-hydroxybenzyl alcohol was added to the reaction vessel, the temperature of the solution was raised to 55 °C, controlled the stirring speed at 130 rpm, added 5mol 3-methyl-2-butanone solution with a mass traction of 86%, 3mol25 samarium oxide powder, raised the temperature of the solution to 69 °C;B: continued to react for 130 min, reduced the temperature of the solution to18 °C, filter, washed with the potassium sulfate solution with a mass fraction of 40% for 5 times, washed with the oxalic acid solution with a mass fraction of 17% for 6 times, washed with the 2-chloro-2-methyl propane solution with a mass fraction of 85% for 7 times, recrystallized in the thiodiglycol solution with a mass fraction of 96%, dehydrated with anhydrous calcium sulfate dehydration, got the finished product p-nitrobenzoic acid.2018100829 19 Jun 2018
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2017105291882 | 2017-07-03 | ||
| CN201710529188.2A CN108238860A (en) | 2017-07-03 | 2017-07-03 | The synthetic method of organic synthesis intermediate 2- amyl-propioladehydes |
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| Publication Number | Publication Date |
|---|---|
| AU2018100829A4 true AU2018100829A4 (en) | 2018-08-02 |
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| AU2018100829A Ceased AU2018100829A4 (en) | 2017-07-03 | 2018-06-19 | Organic synthesis intermediates 2-octanal aldehyde synthesis method |
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| CN (1) | CN108238860A (en) |
| AU (1) | AU2018100829A4 (en) |
| GB (1) | GB201713413D0 (en) |
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2017
- 2017-07-03 CN CN201710529188.2A patent/CN108238860A/en active Pending
- 2017-08-21 GB GBGB1713413.1A patent/GB201713413D0/en not_active Ceased
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2018
- 2018-06-19 AU AU2018100829A patent/AU2018100829A4/en not_active Ceased
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| Publication number | Publication date |
|---|---|
| CN108238860A (en) | 2018-07-03 |
| GB201713413D0 (en) | 2017-10-04 |
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