CN115286490A - Synthetic method of 4,4' -biphenyl dimethyl ether - Google Patents
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- C07C41/01—Preparation of ethers
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- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
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Abstract
The invention discloses a method for synthesizing 4,4' -biphenyl dimethyl ether, which is characterized by comprising the following steps: putting methanol and alkali into a reaction kettle, and stirring and reacting at 20-55 ℃ for 20-40 min; putting 4,4' -biphenyl dichlorobenzyl into a reaction kettle, stirring and reacting for 3-4 h at the temperature of 60-80 ℃, and distilling and recovering methanol; adding water and an extraction solvent into a reaction kettle, stirring and dissolving at 60-70 ℃, standing and layering, discharging the lower-layer water phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing, standing and separating liquid after each water washing, and discharging the water phase out of the reaction kettle to obtain an organic phase; and distilling the organic phase to recover the extraction solvent to obtain the product 4,4' -biphenyl dimethyl ether. According to the invention, through improving the synthesis method and simplifying the post-treatment, the reaction liquid does not need to be taken out of the kettle, the final product does not need to be recrystallized, the yield and the purity of the product are improved, the operation is simple and stable, and the practicability is strong.
Description
Technical Field
The invention belongs to the preparation of organic compounds, and relates to a synthetic method of 4,4' -biphenyl dimethyl ether. The 4,4' -biphenyl dimethyl ether prepared by the method is suitable for being used as a medicine and chemical intermediate.
Background
4,4' -biphenyl dimethyl ether has wide application. It is an important raw material for synthesizing phenolic resin derivatives, and can also be used for synthesizing polymers with low humidity and flame retardance and synthesizing other biphenyl derivatives, especially for synthesizing liquid crystal polymers. Regarding the synthesis method of 4,4' -biphenyldimethyldimethyl ether, there are three main methods reported in the prior art: (1) 4,4' -biphenyl dimethyl ether biphenyl is prepared by a Williamson ether synthesis method by taking 4,4' -biphenyl dichlorobenzyl as a raw material, the method synthesizes the 4,4' -biphenyl dimethyl ether by the biphenyl dichlorobenzyl and methanol under the condition of potassium hydroxide, the reaction time is 3-4 h, and the yield is 75%; (2) The preparation method is characterized by using p-chlorobenzyl methyl ether as a raw material, synthesizing 4,4' -biphenyl dimethyl ether through a coupling reaction in the presence of a Pd/C phase transfer catalyst, wherein the reaction time is 23 hours, and the yield is only 68%; (3) The preparation method is carried out by taking biphenyl as raw material and alkylating on benzene ring, wherein biphenyl and dimethoxymethane are taken as raw materials and are added into zeolite (SiO) 2 /Al 2 O 3 ) 4,4' -biphenyl dimethyl ether was prepared in the presence of the catalyst, but the conversion of biphenyl was only 30% in the process.
In the prior art, compared with the coupling reaction of p-chlorobenzyl methyl ether or the alkylation reaction of biphenyl, the method for synthesizing 4,4' -biphenyl dimethyl ether by using 4,4' -biphenyl dichlorobenzyl as a raw material through Williamson ether synthesis has shorter reaction time and higher yield, but the method needs to add water in the post-treatment process to remove salts generated by the reaction and a small amount of excessive alkali, and partial 4,4' -biphenyl dimethyl ether is lost in the post-treatment process due to mutual solubility of methanol and water, so that the final yield is only 75 percent, and the practicability is poor.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provides a method for synthesizing 4,4' -biphenyl dimethyl ether. The invention takes 4,4' -biphenyl dichlorobenzyl and methanol as raw materials to synthesize 4,4' -biphenyl dimethyl ether under the catalysis of alkali, an extraction solvent is added in the post-treatment process to reduce the solubility of the product in a mixed solution of water and methanol, the materials do not need to be taken out of a kettle after reaction, and the final product does not need to be recrystallized, thereby providing the method for synthesizing the 4,4' -biphenyl dimethyl ether, which simplifies the post-treatment process of synthesis, has simple and stable operation, is beneficial to the control in industrial production, reduces the production energy consumption and cost, has the highest yield of 98 percent and the liquid phase purity of more than 97 percent.
The content of the invention is as follows: a method for synthesizing 4,4' -biphenyl dimethyl ether is characterized by comprising the following steps:
a. putting methanol and alkali into a reaction kettle, and stirring and reacting at the temperature of 20-55 ℃ for 20-40 min;
b. then 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 3 to 4 hours at the temperature of 60 to 80 ℃, and (redundant) methanol is distilled and recycled (namely, most of unreacted methanol in the reaction kettle is removed), so as to obtain a reacted material;
c. adding water and an extraction solvent into a reaction kettle, stirring and dissolving at the temperature of 60-70 ℃, standing to enable an organic phase and a water phase to be layered, discharging the lower water phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 1-3 times, adding water for washing each time, standing for liquid separation, and discharging the water phase out of the reaction kettle to obtain an organic phase; adding water for dissolving alkali and inorganic salt, and adding an extraction solvent for dissolving 4,4' -biphenyldimethyl dimethyl ether and reducing the solubility in a mixed solution of water and methanol;
d. distilling the organic phase to recover the extraction solvent (i.e. removing the extraction solvent in the reaction kettle) to obtain the 4,4' -biphenyl dimethyl ether.
The synthetic method of the 4,4' -biphenyl dimethyl ether comprises the following synthetic route:
the invention comprises the following steps: in the step a, the feeding molar ratio of the alkali to the methanol is 1.
The invention comprises the following steps: the feeding molar ratio of the 4,4' -biphenyl dichlorobenzyl in the step b to the alkali in the step a is 1.
The invention comprises the following steps: the base in step a may be potassium hydroxide, sodium hydroxide or sodium methoxide.
The invention comprises the following steps: the input amount of water in the step c is 0.5 to 8 times of the mass of the materials after the reaction in the step b each time, and the input amount of the extraction solvent in the step c is 0.3 to 8 times of the mass of the materials after the reaction in the step b.
The invention comprises the following steps: the extraction solvent in step c may be: toluene, dichloromethane, dichloroethane, ethyl acetate, and diethyl ether, and toluene is preferred.
Compared with the prior art, the invention has the following characteristics and beneficial effects:
(1) The invention adopts Williamson ether synthesis method to synthesize 4,4' -biphenyl dimethyl ether, and adds extraction solvent in the post-treatment process to reduce the solubility of the product in the mixed solution of water and methanol, thereby reducing the loss of the product in the post-treatment process, avoiding the reaction liquid (material after reaction) from getting out of the kettle, simplifying the synthesis process, improving the yield and purity of the final product, and having simple and stable operation, and being beneficial to the control in the industrial production;
(2) The invention adopts a Williamson ether synthesis method to synthesize 4,4 '-biphenyl dimethyl ether, namely 4,4' -biphenyl dichlorobenzyl and methanol are taken as raw materials to synthesize 4,4 '-biphenyl dimethyl ether under the catalysis of alkali, an extraction solvent and water are adopted for post-treatment, so that reaction liquid (reacted materials) does not need to be taken out of a kettle, and reaction products do not need to be recrystallized, the loss of the products in the post-treatment process is reduced, and the 4,4' -biphenyl dimethyl ether with high purity (the liquid phase purity can reach more than 97 percent) and high yield (the highest can reach 98 percent) is finally obtained;
(3) The invention simplifies the post-synthesis treatment process, has simple preparation process, is suitable for industrial production, reduces the production energy consumption and cost, and has good economic value and strong practicability.
Detailed Description
The following examples are given to further illustrate the present invention and are not to be construed as limiting the scope of the invention, which is intended to be covered by the claims appended hereto.
Example 1:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: putting 2.5L of methanol and 360g of NaOH into a reaction kettle, and stirring and reacting for 30min at the temperature of 30 ℃; then 942g of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 4 hours at the temperature of 70 ℃, and redundant methanol is recovered by distillation; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 60 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 2 times (1L of water is added each time), standing for separating liquid after each water is added for washing, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 97 percent and the liquid phase purity of 98 percent.
Example 2:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: 2.5L of methanol was mixed with 486g of CH 3 Putting ONa into a reaction kettle, and stirring and reacting for 30min at 30 ℃; then 942g of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 3.5 hours at 68 ℃, and redundant methanol is distilled and recycled; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 60 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 2 times (1L of water is added each time), standing for separating liquid after each water is added for washing, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 98 percent and the liquid phase purity of 98 percent.
Example 3:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: putting 2.5L of methanol and 330g of NaOH into a reaction kettle, and stirring and reacting for 30min at the temperature of 30 ℃; then 942g of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 4 hours at the temperature of 70 ℃, and redundant methanol is recovered by distillation; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 50 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle to wash for 2 times (1L of water is added each time), washing with water each time, standing to separate liquid, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 96 percent and the liquid phase purity of 97 percent.
Example 4:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: putting 2.5L of methanol and 375g of NaOH into a reaction kettle, and stirring and reacting for 30min at 30 ℃; then 942g of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 3.5 hours at the temperature of 65 ℃, and redundant methanol is recovered by distillation; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 60 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle to wash for 2 times (1L of water is added each time), washing with water each time, standing to separate liquid, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 98 percent and the liquid phase purity of 98 percent.
Example 5:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: putting 2.5L of methanol and 504g of KOH into a reaction kettle, and stirring and reacting for 30min at the temperature of 30 ℃; 942g of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 4 hours at the temperature of 65 ℃, and redundant methanol is recovered by distillation; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 58 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower-layer aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 2 times (1L of water is added each time), standing for separating liquid after each water is added for washing, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 96 percent and the liquid phase purity of 97 percent.
Example 6:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: 2.5L of methanol was mixed with 450g of CH 3 Putting ONa into a reaction kettle, and stirring and reacting for 30min at 30 ℃; 942g of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 4 hours at 68 ℃, and redundant methanol is recovered by distillation; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 55 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 2 times (1L of water is added each time), standing for separating liquid after each water addition for washing, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 97 percent and the liquid phase purity of 97 percent.
Example 7:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: putting 2.5L of methanol and 470g of KOH into a reaction kettle, and stirring and reacting for 30min at the temperature of 30 ℃; 942g of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 4 hours at the temperature of 70 ℃, and redundant methanol is recovered by distillation; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 58 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 2 times (1L of water is added each time), standing for separating liquid after each water is added for washing, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 96 percent and the liquid phase purity of 97 percent.
Example 8:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: putting 2.5L of methanol and 360g of NaOH into a reaction kettle, and stirring and reacting for 30min at 38 ℃; then 942g of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 3.5 hours at the temperature of 70 ℃, and redundant methanol is recovered by distillation; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 65 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 2 times (1L of water is added each time), standing for separating liquid after each water is added for washing, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 96 percent and the liquid phase purity of 97 percent.
The synthetic method of the 4,4' -biphenyl dimethyl ether comprises the following synthetic route:
example 9:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: putting 2.5L methanol and 360g NaOH into a reaction kettle, and stirring and reacting at 20 ℃ for 40min; 942g of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 4 hours at the temperature of 60 ℃, and redundant methanol is recovered by distillation; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 60 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 2 times (1L of water is added each time), standing for separating liquid after each water is added for washing, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 96 percent and the liquid phase purity of 96 percent.
Example 10:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: 2.5L of methanol was mixed with 486g of CH 3 Putting ONa into a reaction kettle, and stirring and reacting for 20min at 55 ℃; 942g of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 3 hours at the temperature of 80 ℃, and redundant methanol is recovered by distillation; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 70 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 2 times (1L of water is added each time), standing for separating liquid after each water is added for washing, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 98 percent and the liquid phase purity of 98 percent.
Example 11:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: putting 2.5L of methanol and 448g of NaOH into a reaction kettle, and stirring and reacting for 30min at 35 ℃; then, 1.2kg of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 3.5 hours at the temperature of 70 ℃, and redundant methanol is distilled and recovered; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 65 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 2 times (1L of water is added each time), standing for separating liquid after each water is added for washing, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 97 percent and the liquid phase purity of 97 percent.
Example 12:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: putting 2.5L methanol and 616g NaOH into a reaction kettle, and stirring and reacting for 40min at 20 ℃; then 1.8kg of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 4 hours at the temperature of 60 ℃, and redundant methanol is recovered by distillation; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 60 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 2 times (1L of water is added each time), standing for separating liquid after each water is added for washing, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to finally obtain the 4,4' -biphenyl dimethyl ether with the yield of 96 percent and the liquid phase purity of 97 percent.
Example 13:
a method for synthesizing 4,4' -biphenyl dimethyl ether comprises the following steps: 2.5L of methanol was reacted with 476g of CH 3 Putting ONa into a reaction kettle, and stirring and reacting for 20min at 55 ℃; 850g of 4,4' -biphenyl dichlorobenzyl is put into a reaction kettle, stirred and reacted for 3 hours at the temperature of 80 ℃, and redundant methanol is recovered by distillation; adding 1L of water and 0.7L of toluene into a reaction kettle, stirring and dissolving at 70 ℃, standing to separate the organic phase from the aqueous phase, discharging the lower aqueous phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle for washing for 2 times (1L of water is added each time), standing for separating liquid after each water is added for washing, and discharging the aqueous phase out of the reaction kettle; distilling and recovering toluene to obtainThe yield of the 4,4' -biphenyl dimethyl ether is 97 percent, and the liquid phase purity is 97 percent.
In the above embodiment: the percentages used, not specifically indicated, are percentages by weight or known to those skilled in the art; the proportions used, not specifically noted, are mass (weight) proportions; the parts by weight may each be grams or kilograms.
In the above embodiment: the process parameters (temperature, time, etc.) and the numerical values of the components in each step are in the range, and any point can be applicable.
The invention and the technical contents not specifically described in the above examples are the same as those of the prior art, and the raw materials are all commercially available products.
The present invention is not limited to the above-described embodiments, and the present invention can be carried out with the above-described advantageous effects.
Claims (8)
1. A method for synthesizing 4,4' -biphenyl dimethyl ether is characterized by comprising the following steps:
a. putting methanol and alkali into a reaction kettle, and stirring and reacting at the temperature of 20-55 ℃ for 20-40 min;
b. then putting the 4,4' -biphenyl dichlorobenzyl into a reaction kettle, stirring and reacting for 3-4 h at the temperature of 60-80 ℃, and distilling and recovering methanol to obtain a reacted material;
c. adding water and an extraction solvent into the reaction kettle, stirring and dissolving at the temperature of 60-70 ℃, standing to enable the organic phase and the water phase to be layered, discharging the lower-layer water phase out of the reaction kettle, continuously adding water into the organic phase in the reaction kettle to wash for 1-3 times, adding water to wash each time, standing for liquid separation, and discharging the water phase out of the reaction kettle to obtain an organic phase;
d. and distilling the organic phase to recover the extraction solvent to obtain the 4,4' -biphenyl dimethyl ether.
2. The process for synthesizing 4,4' -biphenyldimethyldimethyl ether according to claim 1, wherein: in the step a, the feeding molar ratio of the alkali to the methanol is 1.
3. The process for the synthesis of 4,4' -biphenyldimethyldimethyl ether according to claim 1 or 2, characterized in that: the feeding molar ratio of the 4,4' -biphenyl dichlorobenzyl in the step b to the alkali in the step a is 1.
4. The process for the synthesis of 4,4' -biphenyldimethyldimethyl ether according to claim 1 or 2, characterized in that: in the step a, the alkali is potassium hydroxide, sodium hydroxide or sodium methoxide.
5. A process for the synthesis of 4,4' -biphenyldimethyldimethyl ether according to claim 3, characterized in that: in the step a, the alkali is potassium hydroxide, sodium hydroxide or sodium methoxide.
6. A process for the synthesis of 4,4' -biphenyldimethyldimethyl ether according to claim 1, 2 or 5, characterized in that: the input amount of water in the step c is 0.5 to 8 times of the mass of the materials after the reaction in the step b each time, and the input amount of the extraction solvent in the step c is 0.3 to 8 times of the mass of the materials after the reaction in the step b.
7. A process for the synthesis of 4,4' -biphenyldimethyl-dimethyl-ether according to claim 1, 2 or 5, characterized in that: in the step c, the extraction solvent is any one of toluene, dichloromethane, dichloroethane, ethyl acetate and diethyl ether.
8. The process for synthesizing 4,4' -biphenyldimethyldimethyl ether according to claim 6, wherein: the extraction solvent in step c is any one of toluene, dichloromethane, dichloroethane, ethyl acetate and diethyl ether.
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Citations (2)
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| CN101973855A (en) * | 2010-09-09 | 2011-02-16 | 上海华理生物医药有限公司 | Novel 4,4'-di(alkoxy/aryloxy methyl) biphenyl and preparation thereof |
| CN103288604A (en) * | 2013-05-27 | 2013-09-11 | 潜江新亿宏有机化工有限公司 | Novel process of 1,4-bis(methoxymethyl)-benzene preparation method |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101973855A (en) * | 2010-09-09 | 2011-02-16 | 上海华理生物医药有限公司 | Novel 4,4'-di(alkoxy/aryloxy methyl) biphenyl and preparation thereof |
| CN103288604A (en) * | 2013-05-27 | 2013-09-11 | 潜江新亿宏有机化工有限公司 | Novel process of 1,4-bis(methoxymethyl)-benzene preparation method |
Non-Patent Citations (2)
| Title |
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| MAW-LING WANG等: "Synthesis of novel multi-site phase-transfer catalyst and its application in the reaction of 4,4-bis(chloromethyl)-1,1-biphenyl with 1-butanol", JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 229, pages 259 - 269 * |
| 何海鸥等: "4，4’-二（烷/芳氧基甲基）联苯的合成", 华东理工大学学报（自然科学版）, vol. 37, no. 3, pages 305 - 309 * |
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