AU2018100523A4 - Vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method - Google Patents
Vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method Download PDFInfo
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- AU2018100523A4 AU2018100523A4 AU2018100523A AU2018100523A AU2018100523A4 AU 2018100523 A4 AU2018100523 A4 AU 2018100523A4 AU 2018100523 A AU2018100523 A AU 2018100523A AU 2018100523 A AU2018100523 A AU 2018100523A AU 2018100523 A4 AU2018100523 A4 AU 2018100523A4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
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Abstract
Abstract The present invention discloses vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method by 2-methyl-4-hydroxy-3,6-dimethylol 5 toluene, 2,5-hexanediol solution were added to the reaction vessel, controlled the stirring speed, raising the solution temperature, added molybdenum disulfide powder, raised the temperature of the solution, kept for 90-140 min; extracted with N-methylaniline solution for several times, washed with 2-methylpyridine solution for several times, standing for stratification, recrystallized in 3-methyl-2-butanol solution, 10 dehydrated with dehydrating agent, finally got finished product 2, 3,5-trimethylbenzoquinone.
Description
The present invention discloses vitamin E acetate intermediates
2.3.5- trimethylbenzoquinone synthesis method by 2-methyl-4-hydroxy-3,6-dimethylol 5 toluene, 2,5-hexanediol solution were added to the reaction vessel, controlled the stirring speed, raising the solution temperature, added molybdenum disulfide powder, raised the temperature of the solution, kept for 90-140 min; extracted with N-methylaniline solution for several times, washed with 2-methylpyridine solution for several times, standing for stratification, recrystallized in 3-methyl-2-butanol solution, dehydrated with dehydrating agent, finally got finished product 2,
3.5- trimethylbenzoquinone.
ι
2018100523 24 Apr 2018
Vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method
FIELD OF THE INVENTION
The present invention relates to a method for preparing a pharmaceutical intermediate which belongs to the field of organic synthesis, more particularly, relates to vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method.
GENERAL BACKGROUND
Vitamin E acetate plays a role of preventing the cell membrane and intracellular unsaturated fatty acids and other antioxidants oxidized in metabolic process of the body, so as to protect the integrity of the cell membrane and thus prevent aging in the body. Vitamin E has a strong reduction, it can be used as antioxidants, eliminating free radicals in the body, reducing the damage to the human body. It can be used for skin care, hair care and so on. As a pharmaceutical intermediates of vitamin E acetate, the synthesis method of 2,3,5-trimethylbenzoquinone is of great significance. Most of the existing synthetic methods are using the method that 1,2,4-trimethylbenzene sulfonated with concentrated sulfuric acid to produce 2,4,5-trimethylbenzenesulfonic acid, and then nitrated with potassium nitrate and concentrated sulfuric acid to produce 2,4,5-trimethyl-3,6-dinitrate benzenesulfonic acid potassium, the latter is restored to 2,3,5-trimethyl-p-phenylenediamine dihydrochloride, and then obtained the products that oxidated by sulfuric acid and sodium dichromate. However, this method requires concentrated sulfuric acid and sodium dichromate as reactants, the operation process is very dangerous, environment-friendly coefficient of using concentrated sulfuric acid and sodium dichromate is low, and the synthesis process is more complex. Therefore, it is necessary to propose a new synthetic method.
SUMMARY
Based on the technical problems of the background technology, the purpose of the present invention is to provide vitamin E acetate intermediates
2018100523 24 Apr 2018
2,3,5-trimethylbenzoquinone synthesis method, comprises the following steps:
A: 2-methyl-4-hydroxy-3,6-dimethylol toluene, 2,5-hexanediol solution were added to the reaction vessel, controlled the stirring speed at 190-230 rpm, raising the solution temperature to 40-46 °C, added molybdenum disulfide powder, raised the temperature of the solution to 48-54 °C, kept for 90-140 min;
B: extracted with N-methylaniline solution for several times, washed with
2- methylpyridine solution for several times, standing for stratification, recrystallized in
3- methyl-2-butanol solution, dehydrated with dehydrating agent, finally got finished product 2, 3,5-trimethylbenzoquinone.
Preferably, the 2,5-hexanediol solution has a mass fraction of 60-75%.
Preferably, the mass fraction of the N-methylaniline solution is 80-86%. Preferably, the 2-methylpyridine solution has a mass fraction of 85-89%. Preferably, the 3-methyl-2-butanol solution has a mass fraction of 91-95%. Preferably, the dehydrating agent is any one of anhydrous potassium carbonate and phosphorus pentoxide.
Throughout the reaction process can be the following reaction formula:
hoh2c
Compared with the synthetic method disclosed in the background art, the invention provides vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method, this synthesis method use without concentrated sulfuric acid and sodium dichromate as reactants, the risk coefficient of operation is low, the environment-friendly coefficient is low, avoiding the environmental pollution, reducing intermediate links reaction, decreasing the reaction time and improving 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.
2018100523 24 Apr 2018
DESCRIPTION OF THE DRAWINGS
Figure 1 is the infrared analysis spectrum of finished product 2, 3,5 -trimethylbenzoquinone.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples with reference to specific embodiments of the present invention are further illustrated:
Embodiment 1
Vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method, 10 comprises the following steps:
A: 2 mol 2-methyl-4-hydroxy-3,6-dimethylol toluene, 3mol 2,5-hexanediol solution with a mass fraction of 60% was added to the reaction vessel, controlled the stirring speed at 190 rpm, raising the solution temperature to 40 °C, added 2 mol molybdenum disulfide powder, raised the temperature of the solution to 48 °C, kept for
90 min;
B: extracted with N-methylaniline solution with a mass fraction of 80% for 3 times, washed with 2-methylpyridine solution with a mass fraction of 85% for 5 times, standing for stratification, recrystallized in 3-methyl-2-butanol solution with a mass fraction of 91%, dehydrated with potassium carbonate dehydrating agent, finally got finished product 2, 3,5-trimethylbenzoquinone 523.32g, yield of 89%.
Embodiment 2
Vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method, comprises the following steps:
A: 2 mol 2-methyl-4-hydroxy-3,6-dimethylol toluene, 3.5mol 2,5-hexanediol 25 solution with a mass fraction of 68% was added to the reaction vessel, controlled the stirring speed at 210 rpm, raising the solution temperature to 43 °C, added 2 mol molybdenum disulfide powder, raised the temperature of the solution to 52 °C, kept for
120 min;
B: extracted with N-methylaniline solution with a mass fraction of 83% for 5 30 times, washed with 2-methylpyridine solution with a mass fraction of 87% for 6 times,
2018100523 24 Apr 2018 standing for stratification, recrystallized in 3-methyl-2-butanol solution with a mass fraction of 93%, dehydrated with phosphorus pentoxide dehydrating agent, finally got finished product 2, 3,5-trimethylbenzoquinone 535.08g, yield of 91%.
Embodiment 3
Vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method, comprises the following steps:
A: 2 mol 2-methyl-4-hydroxy-3,6-dimethylol toluene, 4mol 2,5-hexanediol solution with a mass fraction of 75% was added to the reaction vessel, controlled the stirring speed at 230 rpm, raising the solution temperature to 46 °C, added 3 mol molybdenum disulfide powder, raised the temperature of the solution to 54 °C, kept for 140 min;
B: extracted with N-methylaniline solution with a mass fraction of 86% for 7 times, washed with 2-methylpyridine solution with a mass fraction of 89% for 9 times, standing for stratification, recrystallized in 3-methyl-2-butanol solution with a mass fraction of 95%, dehydrated with potassium carbonate dehydrating agent, finally got finished product 2, 3,5-trimethylbenzoquinone 558.6g, yield of 95%.
Infrared analysis of finished product 2, 3,5-trimethylbenzoquinone, infrared spectrum shown in figure 1, the analysis of data as shown in Table 1:
Table 1: Peak data
| Serial | Peak position | Transmittance | Half width | Peak difference |
| number | (cm'1) | (%) | (cnf1) | (%) |
| 1 | 1253 | 48 | 41 | 34 |
| 2 | 1311 | 48 | 34 | 33 |
| 3 | 1384 | 59 | 32 | 26 |
| 4 | 1666 | 9 | 52 | 84 |
| 5 | 2936 | 66 | 38 | 24 |
2018100523 24 Apr 2018
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.
2018100523 24 Apr 2018
Claims (4)
- Claims1. Vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method, comprises the following steps:5 A: 2-methyl-4-hydroxy-3,6-dimethylol toluene, 2,5-hexanediol solution were added to the reaction vessel, controlled the stirring speed at 190-230 rpm, raising the solution temperature to 40-46 °C, added molybdenum disulfide powder, raised the temperature of the solution to 48-54 °C, kept for 90-140 min;B: extracted with N-methylaniline solution for several times, washed with 10 2-methylpyridine solution for several times, standing for stratification, recrystallized in 3-methyl-2-butanol solution, dehydrated with dehydrating agent, finally got finished product 2, 3,5-trimethylbenzoquinone.
- 2. Vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis 15 method according to claim 1 wherein the 2,5-hexanediol solution has a mass fraction of 60-75%.
- 3. Vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method according to claim 1 wherein the mass fraction of the N-methylaniline20 solution is 80-86%..
- 4. Vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method according to claim 1 wherein the 2-methylpyridine solution has a mass fraction of 85-89%.1/12018100523 24 Apr 2018
V — v\ / % If' I η 1 ί 4000 3500 3000 Ξ500 ΞΟΟΟ 1500 1000 500Figure 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710457002.7A CN108238879A (en) | 2017-06-16 | 2017-06-16 | The synthetic method of Vitwas E pharmaceutical intermediate 2,3,5- trimethylbenzoquinones |
| CN2017104570027 | 2017-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2018100523A4 true AU2018100523A4 (en) | 2018-05-24 |
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|---|---|---|---|
| AU2018100523A Ceased AU2018100523A4 (en) | 2017-06-16 | 2018-04-24 | Vitamin E acetate intermediates 2,3,5-trimethylbenzoquinone synthesis method |
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| Country | Link |
|---|---|
| CN (1) | CN108238879A (en) |
| AU (1) | AU2018100523A4 (en) |
| GB (1) | GB201709973D0 (en) |
| IE (1) | IES87022B2 (en) |
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2017
- 2017-06-16 CN CN201710457002.7A patent/CN108238879A/en active Pending
- 2017-06-22 GB GBGB1709973.0A patent/GB201709973D0/en not_active Ceased
-
2018
- 2018-04-04 IE IES20180121A patent/IES87022B2/en unknown
- 2018-04-24 AU AU2018100523A patent/AU2018100523A4/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| IES20180121A2 (en) | 2019-06-12 |
| IES87022B2 (en) | 2019-06-12 |
| CN108238879A (en) | 2018-07-03 |
| GB201709973D0 (en) | 2017-08-09 |
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