CN101985422A - Method for composing p-acetyl methyl benzoate - Google Patents
Method for composing p-acetyl methyl benzoate Download PDFInfo
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- CN101985422A CN101985422A CN2010105179965A CN201010517996A CN101985422A CN 101985422 A CN101985422 A CN 101985422A CN 2010105179965 A CN2010105179965 A CN 2010105179965A CN 201010517996 A CN201010517996 A CN 201010517996A CN 101985422 A CN101985422 A CN 101985422A
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Abstract
The invention discloses a method for composing p-acetyl methyl benzoate. The method comprises the steps of: mixing N,N-dimethylformamide and tetrabutyl ammonium bromide with acetyl bromobenzene, electrolyzing with a constant current after saturating CO2 under constant pressure, and esterifying and steaming the electrolyte so as to obtain the methyl benzoate. Compared with the prior art, the invention has the advantages of simple method, convenient operation, safety, easily-obtained raw materials, low cost, high productivity and environmental protection. Through the method of the invention, the greenhouse gas CO2 is reused efficiently, which not only saves the production cost, but also greatly decreases the atmosphere pollution and mitigates the problem of daily exhausted energy. The invention has a significant sense to protect environment and is operational path having industrial composing value.
Description
Technical field
The present invention relates to the organic chemistry synthesis technical field, specifically a kind of synthetic method to the acetylbenzoic acid methyl esters.
Background technology
To the acetylbenzoic acid methyl esters, English name: methyl 4-acetylbenzoate, molecular formula C
10H
10O
3, molecular weight is 178.18, is a kind of colourless plate crystal, 93～96 ℃ of fusing points have pungency, are slightly soluble in water, are dissolved in alcohol, ketone and ether.To the acetylbenzoic acid methyl esters is a kind of important chemical material, organic synthesis intermediate, the intermediate of fine chemicals and medicament research and development.
At present, relevant preparation to the acetylbenzoic acid methyl esters has following several method by retrieval:
The problem that above public technology exists is a complicated process of preparation, and is not easy to operate, and the intermediate instability that generates, and environment is had pollution.Though to the acetylbenzoic acid methyl esters is unusual important chemical product; but in actual industrial production, do not find very satisfied preparation technology so far yet; up to now, the home and abroad is not seen the report of the chemosynthesis of not only economy but also environmental protection to the acetylbenzoic acid methyl esters as yet.
Summary of the invention
A kind of synthetic method to the acetylbenzoic acid methyl esters of providing at the deficiencies in the prior art is provided, and it adopts electrochemical synthetic technology, and equipment is simple, raw material is easy to get; and it is free from environmental pollution; the productive rate height, cost is low, is a kind of synthetic operational path that is worth of industry that has very much.
The technical scheme that realizes the object of the invention is: a kind of synthetic method to the acetylbenzoic acid methyl esters, be characterized in this method with N, and dinethylformamide, Tetrabutyl amonium bromide and ethanoyl bromobenzene mix, saturated CO under normal pressure
2The back with constant-current electrolysis, electrolytic solution through esterification, revolve and steam the acetylbenzoic acid methyl esters, concrete steps are as follows:
The preparation of a, electrolytic solution
With ethanoyl bromobenzene, Tetrabutyl amonium bromide and N, dinethylformamide is pressed the mixed in molar ratio of 1:1:129, and putting into negative electrode is that silver electrode, anode are the electrolyzer of magnesium rod;
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 3.0～7.0mA/cm
2, constant-current electrolysis, temperature is-15～20 ℃, the energising amount be every mole to ethanoyl bromobenzene 1.6～3.2F, F is a Faraday's number;
C, esterification
Above-mentioned electrolytic solution is mixed by the 25:3:15 volume ratio with Anhydrous potassium carbonate and methyl iodide, is 50～60 ℃ in temperature, 3～5 hours esterifications of stirring and refluxing, and dripping hydrochloric acid neutralizes then, makes the electrolyte ph after the esterification be about 7;
D, revolve steaming
Electrolytic solution after the above-mentioned esterification and ether are pressed the volume ratio extraction three times of 1:1; wash with saturated nacl aqueous solution behind the combined ether layer; the volume ratio of saturated nacl aqueous solution and ether is 1:3; then with the anhydrous magnesium sulfate after-filtration that dewaters; filtrate must be to the acetylbenzoic acid methyl esters after vacuum rotary steam removes ether; the temperature of vacuum rotary steam is 25 ℃, and pressure is 0.1MPa.
It is simple that the present invention compared with prior art has method; easy to operate, safety, raw material is easy to get, and cost is low; the productive rate height; advantage free from environmental pollution, and the greenhouse gases carbonic acid gas carried out effective utilization, not only save production cost; also significantly reduced topsoil; having alleviated the exhausted day by day problem of the energy, environment protection is had very significant meaning, is a kind of synthetic operational path that is worth of industry that has very much.
Embodiment
The present invention is described in further detail by following specific embodiment.
Embodiment 1
The preparation of a, electrolytic solution
With 0.1M(0.1992g) to ethanoyl bromobenzene and 0.1M (0.3222g) tetra-n-butyl ammonium bromide and the analytically pure N of 10 mL, after dinethylformamide mixes, putting into the negative electrode is that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: to the ethanoyl bromobenzene is substrate; N, dinethylformamide are 4
The dried solvent of level molecular sieve; Tetra-n-butyl ammonium bromide is a supporting electrolyte; Tetrabutyl amonium bromide and ethanoyl bromobenzene are analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 5.0mA A/cm
2Current density, temperature is-10 ℃, carries out constant-current electrolysis, the energising amount is 2.0 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309C/mol.
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, stirring and refluxing is 5 hours under 60 ℃ of temperature, esterification is cooled to room temperature with solution after finishing, drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7, its methyl iodide is an analytical pure.
D, revolve steaming
With the used for electrolyte 20mLX3 extracted with diethyl ether after the above-mentioned esterification three times; ether layer in the combining extraction liquid; the extraction liquid ether layer of usefulness 20mL saturated nacl aqueous solution washing merging once again; the ether layer is moved in the Erlenmeyer flask; and in Erlenmeyer flask, add 1.5 hours after-filtration of anhydrous magnesium sulfate drying of about 2.2g, then with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether must product to the acetylbenzoic acid methyl esters; productive rate is 39%, and its ether is an analytical pure.
Embodiment 2
The preparation of a, electrolytic solution
With 0.1M(0.1992g) to ethanoyl bromobenzene and 0.1M (0.3222g) tetra-n-butyl ammonium bromide and the analytically pure N of 10 mL, after dinethylformamide mixes, putting into the negative electrode is that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: to the ethanoyl bromobenzene is substrate; N, dinethylformamide are 4
The dried solvent of level molecular sieve; Tetra-n-butyl ammonium bromide is a supporting electrolyte; Tetrabutyl amonium bromide and ethanoyl bromobenzene are analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 5.0mA A/cm
2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 2.0 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309C/mol.
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, stirring and refluxing is 5 hours under 60 ℃ of temperature, esterification is cooled to room temperature with solution after finishing, drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7, its methyl iodide is an analytical pure.
D, revolve steaming
With the used for electrolyte 20mLX3 extracted with diethyl ether after the above-mentioned esterification three times; ether layer in the combining extraction liquid; the extraction liquid ether layer of usefulness 20mL saturated nacl aqueous solution washing merging once again; the ether layer is moved in the Erlenmeyer flask; and in Erlenmeyer flask, add 1.5 hours after-filtration of about 2.2g anhydrous magnesium sulfate drying, then with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether must product to the acetylbenzoic acid methyl esters; productive rate is 29%, and its ether is an analytical pure.
Embodiment 3
The preparation of a, electrolytic solution
With 0.1M(0.1992g) to ethanoyl bromobenzene and 0.1M (0.3222g) tetra-n-butyl ammonium bromide and the analytically pure N of 10 mL, after dinethylformamide mixes, putting into the negative electrode is that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: to the ethanoyl bromobenzene is substrate; N, dinethylformamide are 4
The dried solvent of level molecular sieve; Tetra-n-butyl ammonium bromide is a supporting electrolyte; Tetrabutyl amonium bromide and ethanoyl bromobenzene are analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 5.0mA A/cm
2Current density, temperature is 10 ℃, carries out constant-current electrolysis, the energising amount is 2.0 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309C/mol.
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, stirring and refluxing is 5 hours under 60 ℃ of temperature, esterification is cooled to room temperature with solution after finishing, drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7, its methyl iodide is an analytical pure.
D, revolve steaming
With the used for electrolyte 20mLX3 extracted with diethyl ether after the above-mentioned esterification three times; ether layer in the combining extraction liquid; the extraction liquid ether layer of usefulness 20mL saturated nacl aqueous solution washing merging once again; the ether layer is moved in the Erlenmeyer flask; and in Erlenmeyer flask, add 1.5 hours after-filtration of about 2.2g anhydrous magnesium sulfate drying, then with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether must product to the acetylbenzoic acid methyl esters; productive rate is 28%, and its ether is an analytical pure.
Embodiment 4
The preparation of a, electrolytic solution
With 0.1M(0.1992g) to ethanoyl bromobenzene and 0.1M (0.3222g) tetra-n-butyl ammonium bromide and the analytically pure N of 10 mL, after dinethylformamide mixes, putting into the negative electrode is that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: to the ethanoyl bromobenzene is substrate; N, dinethylformamide are 4
The dried solvent of level molecular sieve; Tetra-n-butyl ammonium bromide is a supporting electrolyte; Tetrabutyl amonium bromide and ethanoyl bromobenzene are analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 5.0mA A/cm
2Current density, temperature is 20 ℃, carries out constant-current electrolysis, the energising amount is 2.0 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309C/mol.
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, stirring and refluxing is 5 hours under 60 ℃ of temperature, esterification is cooled to room temperature with solution after finishing, drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7, its methyl iodide is an analytical pure.
D, revolve steaming
With the used for electrolyte 20mLX3 extracted with diethyl ether after the above-mentioned esterification three times; ether layer in the combining extraction liquid; the extraction liquid ether layer of usefulness 20mL saturated nacl aqueous solution washing merging once again; the ether layer is moved in the Erlenmeyer flask; and in Erlenmeyer flask, add 1.5 hours after-filtration of about 2.2g anhydrous magnesium sulfate drying, then with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether must product to the acetylbenzoic acid methyl esters; productive rate is 28%, and its ether is an analytical pure.
Embodiment 5
The preparation of a, electrolytic solution
With 0.1M(0.1992g) to ethanoyl bromobenzene and 0.1M (0.3222g) tetra-n-butyl ammonium bromide and the analytically pure N of 10 mL, after dinethylformamide mixes, putting into the negative electrode is that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: to the ethanoyl bromobenzene is substrate; N, dinethylformamide are 4
The dried solvent of level molecular sieve; Tetra-n-butyl ammonium bromide is a supporting electrolyte; Tetrabutyl amonium bromide and ethanoyl bromobenzene are analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 5.0mA A/cm
2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 1.6 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309C/mol.
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, stirring and refluxing is 5 hours under 60 ℃ of temperature, esterification is cooled to room temperature with solution after finishing, drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7, its methyl iodide is an analytical pure.
D, revolve steaming
With the used for electrolyte 20mLX3 extracted with diethyl ether after the above-mentioned esterification three times; ether layer in the combining extraction liquid; the extraction liquid ether layer of usefulness 20mL saturated nacl aqueous solution washing merging once again; the ether layer is moved in the Erlenmeyer flask; and in Erlenmeyer flask, add 1.5 hours after-filtration of about 2.2g anhydrous magnesium sulfate drying, then with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether must product to the acetylbenzoic acid methyl esters; productive rate is 21%, and its ether is an analytical pure.
Embodiment 6
The preparation of a, electrolytic solution
With 0.1M(0.1992g) to ethanoyl bromobenzene and 0.1M (0.3222g) tetra-n-butyl ammonium bromide and the analytically pure N of 10 mL, after dinethylformamide mixes, putting into the negative electrode is that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: to the ethanoyl bromobenzene is substrate; N, dinethylformamide are 4
The dried solvent of level molecular sieve; Tetra-n-butyl ammonium bromide is a supporting electrolyte; Tetrabutyl amonium bromide and ethanoyl bromobenzene are analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 5.0mA A/cm
2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 2.4 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309C/mol.
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, stirring and refluxing is 5 hours under 60 ℃ of temperature, esterification is cooled to room temperature with solution after finishing, drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7, its methyl iodide is an analytical pure.
D, revolve steaming
With the used for electrolyte 20mLX3 extracted with diethyl ether after the above-mentioned esterification three times; ether layer in the combining extraction liquid; the extraction liquid ether layer of usefulness 20mL saturated nacl aqueous solution washing merging once again; the ether layer is moved in the Erlenmeyer flask; and in Erlenmeyer flask, add 1.5 hours after-filtration of about 2.2g anhydrous magnesium sulfate drying, then with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether must product to the acetylbenzoic acid methyl esters; productive rate is 28%, and its ether is an analytical pure.
Embodiment 7
The preparation of a, electrolytic solution
With 0.1M(0.1992g) to ethanoyl bromobenzene and 0.1M (0.3222g) tetra-n-butyl ammonium bromide and the analytically pure N of 10 mL, after dinethylformamide mixes, putting into the negative electrode is that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: to the ethanoyl bromobenzene is substrate; N, dinethylformamide are 4
The dried solvent of level molecular sieve; Tetra-n-butyl ammonium bromide is a supporting electrolyte; Tetrabutyl amonium bromide and ethanoyl bromobenzene are analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 4.0mA A/cm
2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 2.0 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309C/mol.
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, stirring and refluxing is 5 hours under 60 ℃ of temperature, esterification is cooled to room temperature with solution after finishing, drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7, its methyl iodide is an analytical pure.
D, revolve steaming
With the used for electrolyte 20mLX3 extracted with diethyl ether after the above-mentioned esterification three times; ether layer in the combining extraction liquid; the extraction liquid ether layer of usefulness 20mL saturated nacl aqueous solution washing merging once again; the ether layer is moved in the Erlenmeyer flask; and in Erlenmeyer flask, add 1.5 hours after-filtration of about 2.2g anhydrous magnesium sulfate drying, then with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether must product to the acetylbenzoic acid methyl esters; productive rate is 25%, and its methyl iodide is an analytical pure.
Embodiment 8
The preparation of a, electrolytic solution
With 0.1M(0.1992g) to ethanoyl bromobenzene and 0.1M (0.3222g) tetra-n-butyl ammonium bromide and the analytically pure N of 10 mL, after dinethylformamide mixes, putting into the negative electrode is that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: to the ethanoyl bromobenzene is substrate; N, dinethylformamide are 4
The dried solvent of level molecular sieve; Tetra-n-butyl ammonium bromide is a supporting electrolyte; Tetrabutyl amonium bromide and ethanoyl bromobenzene are analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 6.0mA A/cm
2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 2.0 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309C/mol.
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, stirring and refluxing is 5 hours under 60 ℃ of temperature, esterification is cooled to room temperature with solution after finishing, drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7, its methyl iodide is an analytical pure.
D, revolve steaming
With the used for electrolyte 20mLX3 extracted with diethyl ether after the above-mentioned esterification three times; ether layer in the combining extraction liquid; the extraction liquid ether layer of usefulness 20mL saturated nacl aqueous solution washing merging once again; the ether layer is moved in the Erlenmeyer flask; and in Erlenmeyer flask, add 1.5 hours after-filtration of about 2.2g anhydrous magnesium sulfate drying, then with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether must product to the acetylbenzoic acid methyl esters; productive rate is 24%, and its ether is an analytical pure.
More than each embodiment just the present invention will be further described, be not in order to restriction patent of the present invention, all be equivalence enforcement of the present invention, all should be contained within the claim scope of patent of the present invention.
Claims (1)
1. the synthetic method to the acetylbenzoic acid methyl esters is characterized in that this method with N, and dinethylformamide, Tetrabutyl amonium bromide and ethanoyl bromobenzene mix, saturated CO under normal pressure
2The back with constant-current electrolysis, electrolytic solution through esterification, revolve and steam the acetylbenzoic acid methyl esters, concrete steps are as follows:
The preparation of a, electrolytic solution
With ethanoyl bromobenzene, Tetrabutyl amonium bromide and N, dinethylformamide is pressed the mixed in molar ratio of 1:1:129, and putting into negative electrode is that silver electrode, anode are the electrolyzer of magnesium rod;
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 3.0～7.0mA/cm
2, constant-current electrolysis, temperature is-15～20 ℃, the energising amount be every mole to ethanoyl bromobenzene 1.6～3.2F, F is a Faraday's number;
C, esterification
Above-mentioned electrolytic solution is mixed by the 25:3:15 volume ratio with Anhydrous potassium carbonate and methyl iodide, is 50～60 ℃ in temperature, 3～5 hours esterifications of stirring and refluxing, and dripping hydrochloric acid neutralizes then, makes the electrolyte ph after the esterification be about 7;
D, revolve steaming
Electrolytic solution after the above-mentioned esterification and ether are pressed the volume ratio extraction three times of 1:1; wash with saturated nacl aqueous solution behind the combined ether layer; the volume ratio of saturated nacl aqueous solution and ether is 1:3; then with the anhydrous magnesium sulfate after-filtration that dewaters; filtrate must be to the acetylbenzoic acid methyl esters after vacuum rotary steam removes ether; the temperature of vacuum rotary steam is 25 ℃, and pressure is 0.1MPa.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106245054A (en) * | 2016-09-05 | 2016-12-21 | 聊城大学 | A kind of synthetic method of 2 chloro benzoic ethers |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5744021A (en) * | 1995-12-22 | 1998-04-28 | Hoechst Ag | 2-alkylmercapto-4-(trifluoromethyl)benzoic esters and a process for their preparation |
-
2010
- 2010-10-25 CN CN2010105179965A patent/CN101985422A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5744021A (en) * | 1995-12-22 | 1998-04-28 | Hoechst Ag | 2-alkylmercapto-4-(trifluoromethyl)benzoic esters and a process for their preparation |
Non-Patent Citations (1)
| Title |
|---|
| 张凯等: "电化学方法固定CO2用于2-羟基-2-（4-甲氧基苯基）丙酸甲酯的合成", 《高等学校化学学报》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106245054A (en) * | 2016-09-05 | 2016-12-21 | 聊城大学 | A kind of synthetic method of 2 chloro benzoic ethers |
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Application publication date: 20110316 |