AU2018101119A4 - Organic intermediate 1,6-cyclohexanedione synthesis method - Google Patents
Organic intermediate 1,6-cyclohexanedione synthesis method Download PDFInfo
- Publication number
- AU2018101119A4 AU2018101119A4 AU2018101119A AU2018101119A AU2018101119A4 AU 2018101119 A4 AU2018101119 A4 AU 2018101119A4 AU 2018101119 A AU2018101119 A AU 2018101119A AU 2018101119 A AU2018101119 A AU 2018101119A AU 2018101119 A4 AU2018101119 A4 AU 2018101119A4
- Authority
- AU
- Australia
- Prior art keywords
- solution
- cyclohexanedione
- synthesis method
- mass fraction
- organic intermediate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fireproofing Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Organic intermediate 1,6-cyclohexanedione synthesis method Abstract 5 The present invention discloses organic intermediate 1,6-cyclohexanedione synthesis method, comprises the following steps: 2-methoxy-cyclohexanone and nitrile solution are add to the reaction vessel, controls the temperature of the solution, then dimethyl sulfoxide solution is add, controls the stirring speed, continues to react; increases the temperature, sodium nitrate solution and platinum tetrachloride powder 10 is added, reacts, reflux extracted with methylamine solution, combined extraction, washed with potassium sulfate solution, the solution was separated, washed with hexyl ether solution, recrystallized in pentaerythritol solution, dehydrated with dehydration, gets the finished product 1,6-cyclohexanedione.
Description
The present invention discloses organic intermediate 1,6-cyclohexanedione synthesis method, comprises the following steps: 2-methoxy-cyclohexanone and nitrile solution are add to the reaction vessel, controls the temperature of the solution, then dimethyl sulfoxide solution is add, controls the stirring speed, continues to react; increases the temperature, sodium nitrate solution and platinum tetrachloride powder 10 is added, reacts, reflux extracted with methylamine solution, combined extraction, washed with potassium sulfate solution, the solution was separated, washed with hexyl ether solution, recrystallized in pentaerythritol solution, dehydrated with dehydration, gets the finished product 1,6-cyclohexanedione.
ι
2018101119 11 Aug2018
Organic intermediate 1,6-cyclohexanedione 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 intermediate 1,6-cyclohexanedione synthesis method.
GENERAL BACKGROUND
1,6-cyclohexanedione is mainly used as organic synthesis intermediates, the existing synthesis methods are mostly using selenium acid, cyclohexanone, dioxane as 10 reactants, the reaction temperature maintained at 100 °C, and the duration is up to 5 h.
This synthesis method used raw materials selenoic acid, which is a highly toxic compounds, it releases toxic selenium-containing vapor when heating, the health of the operators gets greater harm, the synthesis process is of highly risk factor, it is not conducive to safe production; and the reaction temperature is up to 100 °C, the 15 duration is up to 5h, these reaction conditions will lead to a rapid increase in the energy consumption of the synthesis process, it is not conducive to reducing the cost of synthesis, therefore, it is necessary to propose a new synthesis method.
SUMMARY
Based on the technical problems of the background technology, the purpose of the 20 present invention is to provide organic intermediate 1,6-cyclohexanedione synthesis method, comprises the following steps:
A: 2-methoxy-cyclohexanone and nitrile solution are add to the reaction vessel, controls the temperature of the solution to 40-47 °C for 30-50 min, then dimethyl sulfoxide solution is add, controls the stirring speed at 250-280 rpm, continues to react 25 for 60-80 min;
B: increases the temperature to 50-56 °C, sodium nitrate solution and platinum tetrachloride powder is added, reacts for 2-3 h, reflux extracted with methylamine solution for 40-60 min, combined extraction, washed with potassium sulfate solution for 20-30 min, the solution was separated, washed with hexyl ether solution for 50-60 min, recrystallized in pentaerythritol solution, dehydrated with dehydration, gets the
2018101119 11 Aug 2018 finished product 1,6-cyclohexanedione.
Preferably, the nitrile solution has a mass fraction of 15-22%.
Preferably, the mass fraction of the dimethyl sulfoxide solution Is 30-37%.
Preferably, the sodium nitrate solution lias a mass fraction of 10-16%.
Preferably, the methylamine solution has a mass fraction of 40-45%.
Preferably, the mass traction of potassium sulfate solution is 25-32%.
Preferably, the hexyl ether solution has a mass fraction of 70-76%,
Preferably, the mass fraction of pentaerytliritol solution is 80-85%.
Throughout the reaction process can be the following reaction formula:
Compared with the synthesis method disclosed in the background art, the invention provides organic intermediate 1,6-cyclohexanedione synthesis method, it is unnecessary to use highly toxic compound selenium acid as reactant, avoiding the release of toxic selenium vapor caused by selenite acid heat, which the health of the 15 operator get hazards, the risk factor of synthesis process reduces, it is conducive to safe production; and the reaction temperature requires no longer 100 DC, the duration is also reduced a lot. these changes in reaction conditions are conducive to reducing the energy required tor the synthesis process, it is conducive to reducing the cost of synthesis, reducing intermediate links reaction, decreasing the reaction time and improving the 20 reaction yield, at the same lime, 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 lurther illustrated:
Embodiment 1
Organic intermediate 1,6-cyclohexanedione synthesis method, comprises the following steps:
A: 3mol 2-methoxy-cyclohexanone and nitrile solution with a mass fraction of 15% are add to the reaction vessel, controls the temperature of the solution to 40 °C for 30 min, then 3 mol dimethyl sulfoxide solution with a mass fraction of 30% is add, controls the stirring speed at 250rpm, continues to react for 60 min;
B: increases the temperature to 50 °C, 1.2L sodium nitrate solution with a mass fraction of 10% and 3 mol platinum tetrachloride powder is added, reacts for 2 h, reflux extracted with methylamine solution with a mass fraction of 40% for 40 min, combined extraction, washed with potassium sulfate solution with a mass fraction of 25% for 20 min, the solution was separated, washed with hexyl ether solution with a mass fraction of 70% for 50min, recrystallized in pentaerythritol solution with a mass fraction of 80%, dehydrated with phosphorus pentoxide dehydration, gets the finished product 1,6-cyclohexanedione 327.936g, yield of 97.6%.
Embodiment 2
Organic intermediate 1,6-cyclohexanedione synthesis method, comprises the following steps:
A: 3mol 2-methoxy-cyclohexanone and nitrile solution with a mass fraction of 17.5% are add to the reaction vessel, controls the temperature of the solution to 43.5 °C for 40 min, then 4.5 mol dimethyl sulfoxide solution with a mass fraction of 33.5% is add, controls the stirring speed at 265rpm, continues to react for 70 min;
B: increases the temperature to 53 °C, 1.2L sodium nitrate solution with a mass fraction of 13% and 4.5 mol platinum tetrachloride powder is added, reacts for 2.5 h, reflux extracted with methylamine solution with a mass fraction of 42.5% for 50 min, combined extraction, washed with potassium sulfate solution with a mass fraction of 27.5% for 25 min, the solution was separated, washed with hexyl ether solution with a mass fraction of 73% for 55min, recrystallized in pentaerythritol solution with a mass fraction of 82.5%, dehydrated with anhydrous calcium chloride dehydration, gets the finished product 1,6-cyclohexanedione 328.944g, yield of 97.9%.
Embodiment 3
Organic intermediate 1,6-cyclohexanedione synthesis method, comprises the following steps:
2018101119 11 Aug2018
A: 3mol 2-methoxy-cyclohexanone and nitrile solution with a mass fraction of 22% are add to the reaction vessel, controls the temperature of the solution to 47 °C for 50 min, then 6 mol dimethyl sulfoxide solution with a mass fraction of 37% is add, controls the stirring speed at 280rpm, continues to react for 80 min;
B: increases the temperature to 56 °C, 1.2L sodium nitrate solution with a mass fraction of 16% and 6 mol platinum tetrachloride powder is added, reacts for 3 h, reflux extracted with methylamine solution with a mass fraction of 45% for 60 min, combined extraction, washed with potassium sulfate solution with a mass fraction of 32% for 30 min, the solution was separated, washed with hexyl ether solution with a 10 mass fraction of 76% for 60min, recrystallized in pentaerythritol solution with a mass fraction of 85%, dehydrated with anhydrous calcium chloride dehydration, gets the finished product 1,6-cyclohexanedione 330.288g, yield of 98.3%.
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 15 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.
Claims (5)
1. Organic intermediate 1,6-cyclohexanedione synthesis method, comprises the following steps:
A: 2-methoxy-cyclohexanone and nitrile solution are add to the reaction vessel, controls the temperature of the solution to 40-47 °C for 30-50 min, then dimethyl sulfoxide solution is add, controls the stirring speed at 250-280 rpm, continues to react for 60-80 min;
B: increases the temperature to 50-56 °C, sodium nitrate solution and platinum tetrachloride powder is added, reacts for 2-3 h, reflux extracted with methylamine solution for 40-60 min, combined extraction, washed with potassium sulfate solution for 20-30 min, the solution was separated, washed with hexyl ether solution for 50-60 min, recrystallized in pentaerythritol solution, dehydrated with dehydration, gets the finished product 1,6-cyclohexanedione.
2. Organic intermediate 1,6-cyclohexanedione synthesis method according to claim 1 wherein the nitrile solution has a mass fraction of 15-22%.
3. Organic intermediate 1,6-cyclohexanedione synthesis method according to claim 1 wherein the mass fraction of the dimethyl sulfoxide solution is 30-37%.
4. Organic intermediate 1,6-cyclohexanedione synthesis method according to claim 1 wherein the sodium nitrate solution has a mass fraction of 10-16%.
5. Organic intermediate 1,6-cyclohexanedione synthesis method according to claim 1 wherein the methylamine solution has a mass fraction of 40-45%.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2017107151059 | 2017-08-21 | ||
| CN201710715105.9A CN108238872A (en) | 2017-08-21 | 2017-08-21 | The synthetic method of organic intermediate 1,6- cyclohexanediones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2018101119A4 true AU2018101119A4 (en) | 2018-09-06 |
Family
ID=60117388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2018101119A Ceased AU2018101119A4 (en) | 2017-08-21 | 2018-08-11 | Organic intermediate 1,6-cyclohexanedione synthesis method |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN108238872A (en) |
| AU (1) | AU2018101119A4 (en) |
| GB (1) | GB201714439D0 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108840790A (en) * | 2018-07-31 | 2018-11-20 | 盐城师范学院 | The synthetic method of 1,2- cyclohexanedione |
-
2017
- 2017-08-21 CN CN201710715105.9A patent/CN108238872A/en active Pending
- 2017-09-08 GB GBGB1714439.5A patent/GB201714439D0/en not_active Ceased
-
2018
- 2018-08-11 AU AU2018101119A patent/AU2018101119A4/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CN108238872A (en) | 2018-07-03 |
| GB201714439D0 (en) | 2017-10-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2018101119A4 (en) | Organic intermediate 1,6-cyclohexanedione synthesis method | |
| CN109721545A (en) | A kind of preparation method of azoxystrobin intermediate | |
| CN105669496A (en) | Preparation method of O-methyl isourea sulphate | |
| CN108584992B (en) | Method for preparing anhydrous lithium chloride by gas phase method | |
| AU2018100387A4 (en) | Organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method | |
| CA2797442A1 (en) | Process for the production of ferrous sulphate monohydrate | |
| AU2018100819A4 (en) | Pharmaceutical hormone intermediates 11-ketone-16alpha, 17alpha-epoxy progesterone synthesis method | |
| IES20180277A2 (en) | Organic intermediate 1,6-cyclohexanedione synthesis method | |
| AU2018100823A4 (en) | Drug intermediates 3-ene hexenoic acid synthesis method | |
| CN103232514B (en) | Preparation method of cortisone acetate | |
| AU2018100529A4 (en) | Vitamin K3 drug intermediates 2- menadione synthesis method | |
| AU2018100829A4 (en) | Organic synthesis intermediates 2-octanal aldehyde synthesis method | |
| IES86996B2 (en) | Organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method | |
| AU2018100820A4 (en) | Pharmaceutical intermediates androstane-2,3-break-17-ketone-2, 3-dicarboxylic acid synthesis method | |
| AU2018100419A4 (en) | Organic intermediates dimethylacetic acid synthesis method | |
| CN103254111B (en) | Preparation method of 2,5-dihydropyrrole | |
| AU2018100525A4 (en) | Drug synthesis intermediates p-carboxybenzenesulfonic amide synthesis method | |
| AU2018101111A4 (en) | Organic analytical reagent diphenylcarbazone synthesis method | |
| AU2018101117A4 (en) | Drug intermediates 3-oxoheptanone ethylene glycol synthesis method | |
| AU2018100831A4 (en) | Organic synthesis intermediates 2-tetrolaldehyde synthesis method | |
| AU2018100818A4 (en) | Hormone drug intermediates 9(11)–pregnene-16beta-methyl-17alpha, 21-glycol-3,20-diketone-21-acetate synthesis method | |
| AU2018100533A4 (en) | 3-trichloroacetyl-2, 2-dimethylcyclopropanecarboxylic acid ethyl ester drug synthesis method | |
| AU2018100420A4 (en) | Organic synthesis raw materials valeric acid synthesis method | |
| AU2018101121A4 (en) | Drug intermediates 1,4-pregnenetriene-9α-fluoro-11β,17α,21-triol-3,20- dione-17,21-diacetate synthesis method | |
| AU2018100399A4 (en) | Polyester fiber dyeing modifier isophthalic acid synthesis method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGI | Letters patent sealed or granted (innovation patent) | ||
| MK22 | Patent ceased section 143a(d), or expired - non payment of renewal fee or expiry |