CN103626617A - Method of synthesizing diphenyl-methane derivatives by using benzyl oxides as raw material - Google Patents
Method of synthesizing diphenyl-methane derivatives by using benzyl oxides as raw material Download PDFInfo
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Abstract
The invention discloses a method of synthesizing diphenyl-methane derivatives by using benzyl oxides as raw material. According to the method, various benzyl oxides are used as benzylation agents, boron trifluoride acetic ether is used as a reaction agent, and various arenes are used as raw material and solvents; under the open condition, one-step arene benzylation reaction and concentration, and the purification are conducted to obtain a finished product. The method has a certain universality, better productivity of both electron-donating groups and electron-withdrawing groups of substituted functional groups of substituted arenes and the benzylation agents, and meanwhile, the method has the advantages that the technological conditions are simple, the reaction agents are cheap and easy to get, the production cost is low, the product purification is simple, the environmental pollution is small, and no metal is involved. Through the adoption of the method, a diphenyl-methane derivative product with diversity, high yield and good quality can be prepared. The method can be widely applied to industrialized production of the diphenyl-methane derivatives. Products prepared by adopting the method can be widely used as drug synthesis intermediates, can also be used as essences, aroma solvents, alkalescent dyestuffs and the like, and has a good market application prospect.
Description
Technical field
The invention belongs to organic chemical synthesis technical field, the benzyl that is specifically related to aromatic hydrocarbons is combined to method.
Background technology
Ditane compounds is the important organic synthesis intermediate of a class and industrial chemicals.In medicine and agricultural chemicals are synthetic, commonly use ditane and derivative fragment thereof, as, diphenhydramine is first antihistamine drug in human history, for skin allergy, urticaria, nervous rhinitis etc., is also usually used in preoperative calmness and psychotherapeutics.Industrial, ditane and derivative thereof can be used as perfume compound, the monomer of spices and polycarbonate resin, and dyestuff etc., market application foreground is good.
Ditane and derivative synthesizing process thereof are numerous, often by Friedel-Crafts reaction, linked reaction and reduction reaction, realize.The patent No. is ' method of preparing ditane or derivatives thereof ' patent of 201110211544.9, disclosed method is that to take the immobilized aluminum chloride that chitosan is carrier be catalyzer, derivative and the benzyl chlorine of benzene or benzene of take is raw material, at 75～100 ℃, react, after filtration, underpressure distillation obtains ditane or derivatives thereof.It is few that the method is prepared diphenylmethane derivatives generation waste water, and catalyzer and product are easily separated.But the method still exists weak point:
(1) benzyl reagent is benzyl chlorine, and the scope of reaction is narrower;
(2) immobilized aluminum chloride catalyst needs to prepare under nitrogen protection, and the time is longer, has increased production cost; Aluminum chloride is made catalyzer and is easily caused resultant metal ion residues problem;
(3) by product is hydrochloric acid, stronger to equipment corrosion effect.
Summary of the invention
The object of the invention is the weak point for existing synthesizing diphenyl methane derivative method, a kind of synthetic method of take the diphenylmethane derivatives that benzyl oxide is raw material is provided.Present method has certain universality, no matter replacement functional group for substituted arene and benzyl reagent is that electron-donating group or electron withdrawing group can obtain good productive rate, it is simple that present method has processing condition, reaction reagent is cheaply easy to get, production cost is low, product is purified simple, and environmental pollution is little and without advantages such as metal participations.
The technical scheme that realizes the object of the invention is: a kind of synthetic method of take the diphenylmethane derivatives that benzyl oxide is raw material, take various benzyl oxides as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, aromatic hydrocarbons is raw material and doubles as solvent, under opening condition, through a step Friedel-Crafts reaction, concentrated, the simple process of purifying and finished product.Its concrete grammar step is as follows:
(1) carry out the benzyl glycosylation reaction of aromatic hydrocarbons
Take various benzyl oxides as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, various aromatic hydrocarbons is raw material and doubles as solvent, according to benzyl oxide mmole: boron trifluoride diethyl etherate mmole: the ratio of aromatic hydrocarbons milliliter is 1:(0.2～2): 2 ratio first adds benzyl oxide in reactor, add again aromatic hydrocarbons, under stirring, add again boron trifluoride diethyl etherate, reinforced complete, under opening condition, be warming up to 60～120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution of diphenylmethane derivatives.
Described benzyl oxide is methyl-phenoxide, halo benzyl oxide, methyl substituted benzyl oxide, and aromatic hydrocarbons is toluene, ethylbenzene, dimethylbenzene, trimethylbenzene, naphthalene, anisole etc.
(2) carry out that product is concentrated, purifying
After (1) step completes, the reaction solution of the diphenylmethane derivatives that (1) step is prepared, naturally cooling in air, by the condenser system of dichloromethane rinse reactor, washings is incorporated to the reaction solution in reactor.Then by mixed solution in rotary evaporation concentration response device, collect concentrated solution.Concentrated solution, through purification by silica gel column chromatography, carries out wash-out with elutriant, and the effluent liquid of silica gel column chromatography is concentrated, drains and to obtain product through rotary evaporation.
Described elutriant is sherwood oil.
The present invention adopts after technique scheme, mainly contains following effect:
(1) benzyl oxide raw material sources are extensive, and structure is abundant, are easy to obtain the diphenylmethane derivatives of various functionalization, can meet the multifarious demand of diphenylmethane derivatives kind.
(2) reaction additives boron trifluoride diethyl etherate is cheaply easy to get, and participates in economic environmental protection without metal.
(3) reaction conditions is gentle, save energy; Synthetic operation is easy, and without anhydrous and oxygen-free condition, aftertreatment is simple; With low cost.
(4) reaction times short, yield is better, efficiency is high.
(5) the present invention only needs a step benzyl and the concentrated finished product of purifying to obtain, and good product quality, is convenient to suitability for industrialized production, can meet the demand having a large capacity and a wide range in market.
The inventive method can be widely used in the suitability for industrialized production of diphenylmethane derivatives.Diphenylmethane derivatives can be used as medicinal intermediates, also can be used as spices, aromatic solvent, weakly alkaline dyestuff etc., and market application foreground is good.
Embodiment
Below in conjunction with embodiment, further illustrate the present invention.
Embodiment 1
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are as follows:
(1) take benzyl octyl ether as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, toluene is raw material and doubles as solvent, according to benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio that the ratio of toluene milliliter is 1:0.2:2, in reactor, first add benzyl octyl ether (220.4mg, 1.0mmol), add again toluene (2.0mL), under stirring, add again boron trifluoride diethyl etherate (25 μ L, 0.2mmol), reinforced complete, under opening condition, be warming up to 120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution of benzyl toluene.
After (2) (1) steps complete, the reaction solution of the benzyl toluene that (1) step is prepared, naturally cooling in air, by the condenser system of dichloromethane rinse reactor, washings is incorporated to the reaction solution in reactor.Then by mixed solution in rotary evaporation concentration response device, collect concentrated solution.Concentrated solution, through purification by silica gel column chromatography, carries out wash-out with elutriant, to the effluent liquid of silica gel column chromatography through rotary evaporation concentrate, drain colourless transparent liquid benzyl toluene (45mg, yield 25%, p-:o-:m-=51:39:10).
Described elutriant is sherwood oil.
Embodiment 2
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are with embodiment 1, wherein:
In step (1), take benzyl octyl ether as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, toluene is raw material and doubles as solvent, according to benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio that the ratio of toluene milliliter is 1:2.0:2, in reactor, first add benzyl octyl ether (220.4mg, 1.0mmol), add again toluene (2.0mL), under stirring, add again boron trifluoride diethyl etherate (252 μ L, 2.0mmol), reinforced complete, under opening condition, be warming up to 120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution of benzyl toluene.
In step (2), obtain colourless transparent liquid benzyl toluene (182mg, yield 99%, p-:o-:m-=49:42:9).
Embodiment 3
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are with embodiment 1, wherein:
In step (1), take benzyl octyl ether as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, toluene is raw material and doubles as solvent, according to benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio that the ratio of toluene milliliter is 1:1.2:2, in reactor, first add benzyl octyl ether (220.4mg, 1.0mmol), add again toluene (2.0mL), under stirring, add again boron trifluoride diethyl etherate (151 μ L, 1.2mmol), reinforced complete, under opening condition, be warming up to 120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution of benzyl toluene.
In step (2), obtain colourless transparent liquid benzyl toluene (181mg, yield 99%, p-:o-:m-=50:41:9).
Embodiment 4
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are with embodiment 1, wherein:
In step (1), take benzyl octyl ether as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, toluene is raw material and doubles as solvent, according to benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio that the ratio of toluene milliliter is 1:1.2:2, in reactor, first add benzyl octyl ether (220.4mg, 1.0mmol), add again toluene (2.0mL), under stirring, add again boron trifluoride diethyl etherate (151 μ L, 1.2mmol), reinforced complete, under opening condition, be warming up to 60 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution of benzyl toluene.
In step (2), obtain colourless transparent liquid benzyl toluene (141mg, yield 77%, p-:o-:m-=53:40:7).
Embodiment 5
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are with embodiment 1, wherein:
In step (1), take to luorobenzyl octyl ether is benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, toluene is raw material and doubles as solvent, according to luorobenzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio that the ratio of toluene milliliter is 1:1.2:2, in reactor, first add luorobenzyl octyl ether (238.3mg, 1.0mmol), add again toluene (2.0mL), under stirring, add again boron trifluoride diethyl etherate (151 μ L, 1.2mmol), reinforced complete, under opening condition, be warming up to 120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution to luorobenzyl toluene.
In step (2), obtain colourless transparent liquid to luorobenzyl toluene (193mg, yield 96%, p-:o-:m-=53:40:7).
Embodiment 6
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are with embodiment 1, wherein:
In step (1), take to methyl-benzyl octyl ether is benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, toluene is raw material and doubles as solvent, according to methyl-benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio that the ratio of toluene milliliter is 1:1.2:2, in reactor, first add methyl-benzyl octyl ether (234.4mg, 1.0mmol), add again toluene (2.0mL), under stirring, add again boron trifluoride diethyl etherate (151 μ L, 1.2mmol), reinforced complete, under opening condition, be warming up to 120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution to methyl-benzyl toluene.
In step (2), obtain colourless transparent liquid to methyl-benzyl toluene (153mg, yield 78%, p-:o-:m-=64:32:4).
Embodiment 7
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are with embodiment 1, wherein:
In step (1), take benzyl octyl ether as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, ethylbenzene is raw material and doubles as solvent, according to benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio that the ratio of ethylbenzene milliliter is 1:1.2:2, in reactor, first add benzyl octyl ether (220.4mg, 1.0mmol), add again ethylbenzene (2.0mL), under stirring, add again boron trifluoride diethyl etherate (151 μ L, 1.2mmol), reinforced complete, under opening condition, be warming up to 120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution of benzyl ethylbenzene.
In step (2), obtain colourless transparent liquid benzyl ethylbenzene (159mg, yield 81%, p-:o-:m-=55:35:10).
Embodiment 8
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are with embodiment 1, wherein:
In step (1), take benzyl octyl ether as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, sym-trimethylbenzene is raw material and doubles as solvent, according to benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio that the ratio of sym-trimethylbenzene milliliter is 1:1.2:2, in reactor, first add benzyl octyl ether (220.4mg, 1.0mmol), add again sym-trimethylbenzene (2.0mL), under stirring, add again boron trifluoride diethyl etherate (151 μ L, 1.2mmol), reinforced complete, under opening condition, be warming up to 120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution of benzyl sym-trimethylbenzene.
In step (2), obtain colourless transparent liquid benzyl sym-trimethylbenzene (189mg, yield 89%).
Embodiment 9
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are with embodiment 1, wherein:
In step (1), take diphenyl-methyl octyl ether as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, o-Xylol is raw material and doubles as solvent, according to diphenyl-methyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio that the ratio of o-Xylol milliliter is 1:1.2:2, in reactor, first add diphenyl-methyl octyl ether (296.2mg, 1.0mmol), add again o-Xylol (2.0mL), under stirring, add again boron trifluoride diethyl etherate (151 μ L, 1.2mmol), reinforced complete, under opening condition, be warming up to 120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare diphenyl-methyl (3, 4-dimethyl) reaction solution of benzene.
In step (2), obtain colourless transparent liquid diphenyl-methyl (3,4-dimethyl) benzene (250mg, yield 92%, p->99%).
Embodiment 10
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are with embodiment 1, wherein:
In step (1), take diphenyl-methyl octyl ether as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, phenyl methyl ether is raw material and doubles as solvent, according to diphenyl-methyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio that the ratio of phenyl methyl ether milliliter is 1:1.2:2, in reactor, first add diphenyl-methyl octyl ether (296.2mg, 1.0mmol), add again phenyl methyl ether (2.0mL), under stirring, add again boron trifluoride diethyl etherate (151 μ L, 1.2mmol), reinforced complete, under opening condition, be warming up to 120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution of diphenyl-methyl to anisole.
In step (2), obtain colourless transparent liquid diphenyl-methyl to anisole (266mg, yield 97%, p->99%).
Embodiment 11
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are with embodiment 1, wherein:
In step (1), take benzyl rings hexyl ether as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, toluene is raw material and doubles as solvent, according to benzyl rings hexyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio that the ratio of toluene milliliter is 1:1.2:2, in reactor, first add benzyl rings hexyl ether (190.3mg, 1.0mmol), add again toluene (2.0mL), under stirring, add again boron trifluoride diethyl etherate (151 μ L, 1.2mmol), reinforced complete, under opening condition, be warming up to 120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution of benzyl toluene.
In step (2), obtain colourless transparent liquid benzyl toluene (171mg, yield 94%, p-:o-:m-=53:39:8).
Embodiment 12
A synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, its concrete steps are with embodiment 1, wherein:
In step (1), the positive heptyl ether of the benzyl of take is benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, toluene is raw material and doubles as solvent, according to the positive heptyl ether mmole of benzyl: boron trifluoride diethyl etherate mmole: the ratio that the ratio of toluene milliliter is 1:1.2:2, in reactor, first add the positive heptyl ether (206.3mg of benzyl, 1.0mmol), add again toluene (2.0mL), under stirring, add again boron trifluoride diethyl etherate (151 μ L, 1.2mmol), reinforced complete, under opening condition, be warming up to 120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution of benzyl toluene.
In step (2), obtain colourless transparent liquid benzyl toluene (159mg, yield 87%, p-:o-:m-=52:41:7).
Embodiment 13-31
Concrete steps for the synthetic method of the diphenylmethane derivatives that the benzyl oxide of take is raw material, with embodiment 1, different piece is wherein as shown in the table.
Table 1
Claims (10)
1. a synthetic method for the diphenylmethane derivatives that the benzyl oxide of take is raw material, is characterized in that concrete method steps is as follows:
(1) carry out the benzyl glycosylation reaction of aromatic hydrocarbons
Take various benzyl oxides as benzyl reagent, boron trifluoride diethyl etherate is reaction reagent, various aromatic hydrocarbons is raw material and doubles as solvent, according to benzyl oxide mmole: boron trifluoride diethyl etherate mmole: the ratio of aromatic hydrocarbons milliliter is 1:(0.2～2): 2 ratio first adds benzyl oxide in reactor, add again aromatic hydrocarbons, under stirring, add again boron trifluoride diethyl etherate, reinforced complete, under opening condition, be warming up to 60～120 ℃ of lasting stirrings and carry out benzyl glycosylation reaction 2 hours, prepare the reaction solution of diphenylmethane derivatives;
Described benzyl oxide is methyl-phenoxide, halo benzyl oxide, methyl substituted benzyl oxide, and aromatic hydrocarbons is toluene, ethylbenzene, dimethylbenzene, trimethylbenzene, naphthalene, anisole etc.;
(2) carry out that product is concentrated, purifying
After (1) step completes, the reaction solution of the diphenylmethane derivatives that (1) step is prepared, naturally cooling in air, by the condenser system of dichloromethane rinse reactor, washings is incorporated to the reaction solution in reactor; Then by mixed solution in rotary evaporation concentration response device, collect concentrated solution; Concentrated solution, through purification by silica gel column chromatography, carries out wash-out with elutriant, and the effluent liquid of silica gel column chromatography is concentrated, drains and to obtain product through rotary evaporation;
Described elutriant is sherwood oil.
2. according to a kind of synthetic method of take the diphenylmethane derivatives that benzyl oxide is raw material claimed in claim 1, it is characterized in that: in step (1), benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio of toluene milliliter is 1:0.2:2, is warming up to 120 ℃ of lasting stirrings and carries out benzyl glycosylation reaction 2 hours;
In step (2), obtain colourless transparent liquid benzyl toluene.
3. according to a kind of synthetic method of take the diphenylmethane derivatives that benzyl oxide is raw material claimed in claim 1, it is characterized in that: in step (1), benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio of toluene milliliter is 1:2.0:2, is warming up to 120 ℃ of lasting stirrings and carries out benzyl glycosylation reaction 2 hours;
In step (2), obtain colourless transparent liquid benzyl toluene.
4. according to a kind of synthetic method of take the diphenylmethane derivatives that benzyl oxide is raw material claimed in claim 1, it is characterized in that: in step (1), benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio of toluene milliliter is 1:1.2:2, is warming up to 120 ℃ of lasting stirrings and carries out benzyl glycosylation reaction 2 hours;
In step (2), obtain colourless transparent liquid benzyl toluene.
5. according to a kind of synthetic method of take the diphenylmethane derivatives that benzyl oxide is raw material claimed in claim 1, it is characterized in that: in step (1), benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio of toluene milliliter is 1:1.2:2, is warming up to 60 ℃ of lasting stirrings and carries out benzyl glycosylation reaction 2 hours;
In step (2), obtain colourless transparent liquid benzyl toluene.
6. according to a kind of synthetic method of take the diphenylmethane derivatives that benzyl oxide is raw material claimed in claim 1, it is characterized in that: in step (1), to luorobenzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio of toluene milliliter is 1:1.2:2, is warming up to 120 ℃ and continues to stir and carry out benzyl glycosylation reaction 2 hours;
In step (2), obtain colourless transparent liquid to luorobenzyl toluene.
7. according to a kind of synthetic method of take the diphenylmethane derivatives that benzyl oxide is raw material claimed in claim 1, it is characterized in that: in step (1), to methyl-benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio of toluene milliliter is 1:1.2:2, is warming up to 120 ℃ and continues to stir and carry out benzyl glycosylation reaction 2 hours;
In step (2), obtain colourless transparent liquid to methyl-benzyl toluene.
8. according to a kind of synthetic method of take the diphenylmethane derivatives that benzyl oxide is raw material claimed in claim 1, it is characterized in that: in step (1), benzyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio of ethylbenzene milliliter is 1:1.2:2, is warming up to 120 ℃ of lasting stirrings and carries out benzyl glycosylation reaction 2 hours;
In step (2), obtain colourless transparent liquid benzyl ethylbenzene.
9. according to a kind of synthetic method of take the diphenylmethane derivatives that benzyl oxide is raw material claimed in claim 1, it is characterized in that: in step (1), diphenyl-methyl octyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio of phenyl methyl ether milliliter is 1:1.2:2, is warming up to 120 ℃ of lasting stirrings and carries out benzyl glycosylation reaction 2 hours;
In step (2), obtain colourless transparent liquid diphenyl-methyl to anisole.
10. according to a kind of synthetic method of take the diphenylmethane derivatives that benzyl oxide is raw material claimed in claim 1, it is characterized in that: in step (1), benzyl rings hexyl ether mmole: boron trifluoride diethyl etherate mmole: the ratio of toluene milliliter is 1:1.2:2, is warming up to 120 ℃ of lasting stirrings and carries out benzyl glycosylation reaction 2 hours;
In step (2), obtain colourless transparent liquid benzyl toluene.
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| CN104447154A (en) * | 2014-12-05 | 2015-03-25 | 重庆大学 | Method for removing hydroxy (mercapto), alkoxy, acetyl and allyloxy groups |
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| HUI YU, TAO WU, CHAOZHONG LI: "onverting Radical Oligomers to a Single Product", 《J.AM.CHEM.SOC.》 * |
| JIN-WEN HUANG, MIN SHI: "Lewis acid BF3·OEt2-catalyzed Friedel–Crafts reaction of methylenecyclopropanes with arenes", 《TETRAHEDRON LETT.》 * |
| 王池雅等: "二苯甲烷合成研究进展", 《轻工科技》 * |
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| CN104447154A (en) * | 2014-12-05 | 2015-03-25 | 重庆大学 | Method for removing hydroxy (mercapto), alkoxy, acetyl and allyloxy groups |
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