CN110483301A - A kind of preparation method of 2- oxo-pentane -1,5- dicarboxylate - Google Patents
A kind of preparation method of 2- oxo-pentane -1,5- dicarboxylate Download PDFInfo
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- CN110483301A CN110483301A CN201810619467.2A CN201810619467A CN110483301A CN 110483301 A CN110483301 A CN 110483301A CN 201810619467 A CN201810619467 A CN 201810619467A CN 110483301 A CN110483301 A CN 110483301A
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- China
- Prior art keywords
- oxo
- dicarboxylate
- preparation
- pentane
- ion exchange
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Abstract
The invention discloses a kind of 2- oxo-pentanes -1, the preparation method of 5- dicarboxylate, ethyl alcohol, a-KG, catalyst are sequentially added into reaction flask, system is after mixing, stirring at normal temperature reaction, reaction solution filtering, is concentrated to get 2- oxo-pentane -1,5- dicarboxylate, wherein the molar ratio of ethyl alcohol and a-KG is 15:1~1.2；Wherein, the catalyst is ion exchange resin Amberlyst-15, and the mass ratio of the ion exchange resin Amberlyst-15 and a-KG is 1:2~2.2.This preparation method reaction condition is mild, and preparation process and purification step are simple and direct safely, and product yield is high, is easy to implement industrialization.
Description
Technical field
The present invention relates to compound synthesis technical field more particularly to a kind of 2- oxo-pentane -1,5- dicarboxylates
Preparation method.
Background technique
2- oxo-pentane -1,5- dicarboxylate is fat compound research, exploitation and most widely used kind
One of.As important fine chemical material, it is related to medicine, pesticide, the various aspects such as feed.Especially nearest twenty or thirty year
Significant quantities of fat class medicinal activity intermediate is found, so that being in the development of blowout, fats to the exploitation of fat compound
Reactive intermediate is the hot product studied from now on.Document Journal of Medicinal Chemistry, 60 (21),
9090-9096；A kind of method that ethyl ester is generated as raw material using chloroacetic chloride is disclosed in 2017, there is high risk, is had strong smelly
Taste, chloroacetic chloride are that a kind of corrosive agent has stronger irritation to eyes.In addition to this, which need to carry out at low temperature, in work
There is quite high risk in industry production, environmental pollution is very serious.
Summary of the invention
The purpose of the present invention is to defects present in existing ethyl ester production method, provide a kind of 2- oxo-pentane-
The preparation method of 1,5- dicarboxylate, reaction condition is mild, and preparation process and purification step are safe and simple, environmentally protective,
It is suitble to industrialized production.
To achieve the goals above, the present invention adopts the following technical scheme:
A kind of preparation method of 2- oxo-pentane -1,5- dicarboxylate, ethyl alcohol, 2- oxygen are sequentially added into reaction flask
For glutaric acid, catalyst, system after mixing, is stirred to react 1~2 hour at 20~30 DEG C, stops reaction, reaction solution mistake
Filter, be concentrated to get 2- oxo-pentane -1,5- dicarboxylate, wherein the molar ratio of ethyl alcohol and a-KG be 15:1~
1.2。
Wherein, the catalyst is ion exchange resin Amberlyst-15, the ion exchange resin Amberlyst-
15 with the mass ratio of a-KG be 1:2~2.2.
Compared with prior art, the present invention realize the utility model has the advantages that a kind of preparation side of 1- ethyl -3- nitrobenzene of the present invention
In method, reaction condition is mild, and preparation process and purification step are simple and direct safely, and product yield is high, is easy to implement industrialization.
Specific embodiment
In order to illustrate more clearly of technical solution of the present invention, it is further described below in conjunction with each embodiment.
It is as follows to prepare a kind of process route that 2- oxo-pentane -1,5- dicarboxylate is related to:
Embodiment 1
250 milliliters of ethyl alcohol is added in the three products bottle of 500mL, sequentially add at room temperature a-KG (43.8g,
0.3mol, 1.0eq), Amberlyst15 (wet type, ion exchange resin) (22g) is stirred to react 1 hour after adding, TLC with
Track monitoring reaction terminates.2- oxo-pentane -1,5- dicarboxylate 57.8g, yield will be obtained after reaction solution filtering and concentrating
95%.
Nuclear magnetic data: 1H NMR (400M Hz, CDCl3)
δ=1.24 (t, 3H), 1.24 (t, 3H)；2.65(t,2H)；3.14(t,2H)；4.13(q,2H)；4.32(q,2H).
Embodiment 2
100 milliliters of ethyl alcohol is added in the three products bottle of 250mL, sequentially add at room temperature a-KG (14.6g,
0.1mol, 1.0eq), Amberlyst15 (wet type, ion exchange resin) (15g) is stirred to react 1 hour after adding, TLC with
Track monitoring reaction terminates.Product 18.2g, yield 90.8% will be obtained after reaction solution filtering and concentrating.
Nuclear magnetic data: 1H NMR (400M Hz, CDCl3)
δ=1.24 (t, 3H), 1.24 (t, 3H)；2.65(t,2H)；3.14(t,2H)；4.13(q,2H)；4.32(q,2H).
Embodiment 3
100 milliliters of ethyl alcohol is added in the three products bottle of 250mL, sequentially add at room temperature a-KG (14.6g,
0.1mol, 1.0eq), Amberlyst15 (wet type, ion exchange resin) (8g) is stirred to react 1 hour at 80 DEG C after adding,
The reaction of TLC tracking and monitoring terminates.Product 19.1g, yield 94.9% will be obtained after reaction solution filtering and concentrating.
Nuclear magnetic data: 1H NMR (400M Hz, CDCl3)
δ=1.24 (t, 3H), 1.24 (t, 3H)；2.65(t,2H)；3.14(t,2H)；4.13(q,2H)；4.32(q,2H).
The above specific embodiments are only exemplary, is to preferably make skilled artisans appreciate that originally
Patent, be not to be construed as include to this patent range limitation；As long as appointing made by the spirit according to disclosed in this patent
How with change or modification, the range that this patent includes is each fallen within.
Claims (2)
1. a kind of preparation method of 2- oxo-pentane -1,5- dicarboxylate, which is characterized in that sequentially added into reaction flask
Ethyl alcohol, a-KG, catalyst, system after mixing, are stirred to react 1~2 hour, reaction solution mistake at 20~30 DEG C
Filter, be concentrated to get 2- oxo-pentane -1,5- dicarboxylate, wherein the molar ratio of ethyl alcohol and a-KG be 15:1~
1.2。
2. a kind of preparation method of 2- oxo-pentane -1,5- dicarboxylate as described in claim 1, which is characterized in that
The catalyst is ion exchange resin Amberlyst-15, the ion exchange resin Amberlyst-15 and 2- oxo penta 2
The mass ratio of acid is 1:2~2.2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810619467.2A CN110483301A (en) | 2018-06-11 | 2018-06-11 | A kind of preparation method of 2- oxo-pentane -1,5- dicarboxylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810619467.2A CN110483301A (en) | 2018-06-11 | 2018-06-11 | A kind of preparation method of 2- oxo-pentane -1,5- dicarboxylate |
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| Publication Number | Publication Date |
|---|---|
| CN110483301A true CN110483301A (en) | 2019-11-22 |
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ID=68544957
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|---|---|---|---|
| CN201810619467.2A Pending CN110483301A (en) | 2018-06-11 | 2018-06-11 | A kind of preparation method of 2- oxo-pentane -1,5- dicarboxylate |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060252956A1 (en) * | 2004-07-19 | 2006-11-09 | Board Of Trustees Of Michigan State University | Process for reactive esterification distillation |
| US20070004653A1 (en) * | 2005-05-11 | 2007-01-04 | Roberto Arosio | Stable lyophilized anthracycline glycosides |
| CN106242970A (en) * | 2016-08-03 | 2016-12-21 | 中国石油大学(华东) | A kind of Apparatus and method for producing dimethyl adipate |
-
2018
- 2018-06-11 CN CN201810619467.2A patent/CN110483301A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060252956A1 (en) * | 2004-07-19 | 2006-11-09 | Board Of Trustees Of Michigan State University | Process for reactive esterification distillation |
| US20070004653A1 (en) * | 2005-05-11 | 2007-01-04 | Roberto Arosio | Stable lyophilized anthracycline glycosides |
| CN106242970A (en) * | 2016-08-03 | 2016-12-21 | 中国石油大学(华东) | A kind of Apparatus and method for producing dimethyl adipate |
Non-Patent Citations (4)
| Title |
|---|
| JAMES T. SLAMA ET AL.: "An Approach to Trapping 7-Glutamyl Radical Intermediates Proposed for Vitamin K Dependent Carboxylase: ,/3-Methyleneglutamic Acid", 《J. MED. CHEM.》 * |
| 曹莉莲等: "Amberlyst15强酸性树脂在精细有机合成中的应用", 《北京工商大学学报》 * |
| 李平等: "催化酯化合成己二酸二甲酯", 《山东化工》 * |
| 王丹君等: "固体酸催化剂在酯化反应中的研究进展", 《山东化工》 * |
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Application publication date: 20191122 |