AU2018100531A4 - Mandelic acid drug intermediate benzaldehyde synthesis method - Google Patents
Mandelic acid drug intermediate benzaldehyde synthesis method Download PDFInfo
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- AU2018100531A4 AU2018100531A4 AU2018100531A AU2018100531A AU2018100531A4 AU 2018100531 A4 AU2018100531 A4 AU 2018100531A4 AU 2018100531 A AU2018100531 A AU 2018100531A AU 2018100531 A AU2018100531 A AU 2018100531A AU 2018100531 A4 AU2018100531 A4 AU 2018100531A4
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- 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
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Abstract
Abstract The present invention discloses mandelic acid drug intermediate benzaldehyde synthesis method, comprises the following steps: 1-methyl-6-hydroxy benzene, 5 potassium chloride solution were added to the reaction vessel, controlled the stirring speed, raised temperature, kept reflux, reduced temperature,added glycerol diacetate solution; added the lutetium oxide in batches, continued to react, added the potassium nitrate solution, standing still for layer, removing oil layer, washed with pentylformate solution and chloroacetonitrile solution, recrystallized in the 2-chlorinated ethanol 10 solution, dehydrated with dehydration, got the finished product benzaldehyde.
Description
The present invention discloses mandelic acid drug intermediate benzaldehyde synthesis method, comprises the following steps: 1-methyl-6-hydroxy benzene, potassium chloride solution were added to the reaction vessel, controlled the stirring speed, raised temperature, kept reflux, reduced temperature,added glycerol diacetate solution; added the lutetium oxide in batches, continued to react, added the potassium nitrate solution, standing still for layer, removing oil layer, washed with pentylformate solution and chloroacetonitrile solution, recrystallized in the 2-chlorinated ethanol solution, dehydrated with dehydration, got the finished product benzaldehyde.
2018100531 24 Apr 2018
Mandelic acid drug intermediate benzaldehyde synthesis method
FIELD OF THE INVENTION
The present invention relates to a medicine intermediate method which belongs to 5 the field of organic synthesis, more particularly, relates to mandelic acid drug intermediate benzaldehyde synthesis method.
GENERAL BACKGROUND
Benzaldehyde is an important raw material for medicine, dyestuff, spice and resin industry. It can be used as solvent, plasticizer and temperature lubricant. It is mainly used for the preparation of edible essence in essence industry, a small amount for the flavor of the essence and tobacco flavor. Although it is widely used as a commercial food condiment and industrial solvent, the main use of benzaldehyde is still used for synthesizing various other compounds from medical medicine to plastic additives.
Benzaldehyde is also an important intermediate product for the production of perfumes, spices and synthetic certain aniline dyes. The synthesis of mandelic acid use the benzaldehyde as initial reagent, the hydrocyanic acid reacts with the benzaldehyde, then the product mandelonitrile is hydrolyzed racemic mandelic acid. Most of the existing synthesis methods are using the process that benzene and aluminum chloride react with carbon monoxide and hydrogen chloride under pressure. This method of production requires the condition of pressure reaction and carbon monoxide and hydrogen chloride as reactants, reaction energy consumption is high, carbon monoxide and hydrogen chloride are poisonous gas, and flammable and explosive, the synthesis process is of high risks, 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 mandelic acid drug intermediate benzaldehyde synthesis method, comprises the following steps:
2018100531 24 Apr 2018
A: l-methyl-6-hydroxy benzene, 1.3L potassium chloride solution were added to the reaction vessel, controlled the stirring speed at 210-250 rpm, raised temperature to 60-68°C, kept reflux for 80-110 min, reduced temperature to 30-37°C,added glycerol diacetate solution;
B: added the lutetium oxide in batches within 30-50min, continued to react for 60-80 min, added the potassium nitrate solution, standing still for layer, removing oil layer, washed with pentylformate solution and chloroacetonitrile solution, recrystallized in the 2-chlorinated ethanol solution, dehydrated with dehydration, got the finished product benzaldehyde.
Preferably, the potassium chloride solution has a mass fraction of 20-26%.
Preferably, the mass fraction of the glycerol diacetate solution is 40-45%.
Preferably, the potassium nitrate solution has a mass fraction of 10-15%.
Preferably, the pentylformate solution has a mass fraction of 50-57%.
Preferably, the mass fraction of chloroacetonitrile solution is 60-66%.
Preferably, the mass fraction of 2-chlorinated ethanol solution is 80-87%.
Throughout the reaction process can be the following reaction formula:
CHO
CH2NH2
C7H|2O5 + Lu2O3
Compared with the synthesis method disclosed in the background art, the invention mandelic acid drug intermediate benzaldehyde synthesis method, it is unnecessary to react under pressure, reducing the energy consumption of reaction, and to use carbon monoxide and hydrogen chloride as reactants, avoiding the carbon monoxide and hydrogen chloride which belong to poisonous gas bring the flammable and explosive risk, reduces the factor of risk, 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.
2018100531 24 Apr 2018
DESCRIPTION OF THE DRAWINGS
Figure 1 is the 3CNMR analysis spectrum of finished product benzaldehyde. Figure 2 is a map of the atomic number of benzaldehyde molecule.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples with reference to specific embodiments of the present invention are further illustrated:
Embodiment 1
Mandelic acid drug intermediate benzaldehyde synthesis method, comprises the 10 following steps:
A: 2mol l-methyl-6-hydroxy benzene, 1.3L potassium chloride solution with a mass fraction of 20%, controlled the stirring speed at 210rpm, raised temperature to 60 °C , kept reflux for 80min, reduced temperature to 30 °C,added 3mol glycerol diacetate solution with a mass fraction of 40%;
B: added 2mol lutetium oxide at three times within 30min, continued to react
60min, added the potassium nitrate solution with a mass fraction of 10%, standing still for layer, removing oil layer, washed with pentylformate solution with a mass fraction of 50% and chloroacetonitrile solution with a mass fraction of 60%, recrystallized in the 2-chlorinated ethanol solution with a mass fraction of 80%, dehydrated with anhydrous sodium sulfate dehydration, got the finished product benzaldehyde 186.55g, yield of 88%.
Embodiment 2
Mandelic acid drug intermediate benzaldehyde synthesis method, comprises the following steps:
A: 2mol l-methyl-6-hydroxy benzene, 1.3L potassium chloride solution with a mass fraction of 23%, controlled the stirring speed at 230rpm, raised temperature to 63°C, kept reflux for 90min, reduced temperature to 33°C,added 3.5mol glycerol diacetate solution with a mass fraction of 42%;
2018100531 24 Apr 2018
B: added 2.5mol lutetium oxide at five times within 40min, continued to react 70min, added the potassium nitrate solution with a mass fraction of 12%, standing still for layer, removing oil layer, washed with pentylformate solution with a mass fraction of 53% and chloroacetonitrile solution with a mass fraction of 63%, recrystallized in the
2-chlorinated ethanol solution with a mass fraction of 83%, dehydrated with anhydrous calcium sulphate dehydration, got the finished product benzaldehyde 195.04g, yield of 92%.
Embodiment 3
Mandelic acid drug intermediate benzaldehyde synthesis method, comprises the following steps:
A: 2mol l-methyl-6-hydroxy benzene, 1.3L potassium chloride solution with a mass fraction of 26%, controlled the stirring speed at 250rpm, raised temperature to 68°C, kept reflux for HOmin, reduced temperature to 37°C,added 4mol glycerol diacetate solution with a mass fraction of 45%;
B: added 3mol lutetium oxide at seven times within 50min, continued to react 80min, added the potassium nitrate solution with a mass fraction of 15%, standing still for layer, removing oil layer, washed with pentylformate solution with a mass fraction of 57% and chloroacetonitrile solution with a mass fraction of 66%, recrystallized in the
2-chlorinated ethanol solution with a mass fraction of 87%, dehydrated with anhydrous potassium carbonate dehydration, got the finished product benzaldehyde 199.28g, yield of 94%.
The 13CNMR analysis of the finished product benzaldehyde is shown in figure 1. The atomic number mark of the finished product benzaldehyde molecule is shown in figure 2.
The analysis data is shown in table 1.
2018100531 24 Apr 2018
Table 1 Analysis data
| Chemical shift | Spectral peak area integral | Atomic number |
| 192.28 | 463 | 5 |
| 136.47 | 211 | 4 |
| 134.43 | 423 | 3 |
| 129.68 | 1000 | 2 |
| 128.98 | 976 | 1 |
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.
2018100531 24 Apr 2018
Claims (2)
- Claims1. Mandelic acid drug intermediate benzaldehyde synthesis method, comprises the following steps:5 A: l-methyl-6-hydroxy benzene, 1.3L potassium chloride solution were added to the reaction vessel, controlled the stirring speed at 210-250 rpm, raised temperature to 60-68°C, kept reflux for 80-110 min, reduced temperature to 30-37°C,added glycerol diacetate solution;B: added the lutetium oxide in batches within 30-50min, continued to react for 10 60-80 min, added the potassium nitrate solution, standing still for layer, removing oil layer, washed with pentylformate solution and chloroacetonitrile solution, recrystallized in the 2-chlorinated ethanol solution, dehydrated with dehydration, got the finished product benzaldehyde.15 2. Mandelic acid drug intermediate benzaldehyde synthesis method according to claim 1 wherein the potassium chloride solution has a mass fraction of 20-26%.3. Mandelic acid drug intermediate benzaldehyde synthesis method according to claim 1 wherein the mass fraction of the glycerol diacetate solution is 40-45%.4. Mandelic acid drug intermediate benzaldehyde synthesis method according to claim 1 wherein the potassium nitrate solution has a mass fraction of 10-15%.1/12018100531 24Apr2018
I ' I 1 T“ 1 1 1 1 1 1 1 1 1 1 1 1 H 200 180 160 140 120 100 SO 60 40 20 0 ppmFigure 1Figure 2 - 2^
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710457420.6A CN108238859A (en) | 2017-06-18 | 2017-06-18 | The synthetic method of mandelic acid pharmaceutical intermediate benzaldehyde |
| CN2017104574206 | 2017-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2018100531A4 true AU2018100531A4 (en) | 2018-06-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2018100531A Ceased AU2018100531A4 (en) | 2017-06-18 | 2018-04-24 | Mandelic acid drug intermediate benzaldehyde synthesis method |
Country Status (4)
| Country | Link |
|---|---|
| CN (1) | CN108238859A (en) |
| AU (1) | AU2018100531A4 (en) |
| GB (1) | GB201710735D0 (en) |
| IE (1) | IES20180116A2 (en) |
-
2017
- 2017-06-18 CN CN201710457420.6A patent/CN108238859A/en active Pending
- 2017-07-04 GB GBGB1710735.0A patent/GB201710735D0/en not_active Ceased
-
2018
- 2018-04-04 IE IES20180116 patent/IES20180116A2/en not_active Application Discontinuation
- 2018-04-24 AU AU2018100531A patent/AU2018100531A4/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| GB201710735D0 (en) | 2017-08-16 |
| IES20180116A2 (en) | 2019-11-13 |
| CN108238859A (en) | 2018-07-03 |
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