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Method of synthesizing diphenyl-methane derivatives by using benzyl oxides as raw material

A technology for diphenylmethane and a synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, condensation between hydrocarbons and non-hydrocarbons to produce hydrocarbons, etc., can solve the problem of residual metal ions in products, strong corrosion of equipment, and increase in production costs. and other problems, to achieve the effect of good product quality, short response time and energy saving

Inactive Publication Date: 2015-05-13
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] (1) benzylation reagent is benzyl chloride, and the scope of reaction is narrower;
[0005] (2) The immobilized aluminum chloride catalyst needs to be prepared under the protection of nitrogen, which takes a long time and increases the production cost; aluminum chloride is used as a catalyst to easily lead to the problem of residual metal ions in the product;
[0006] (3) The by-product is hydrochloric acid, which has a strong corrosion effect on equipment

Method used

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  • Method of synthesizing diphenyl-methane derivatives by using benzyl oxides as raw material
  • Method of synthesizing diphenyl-methane derivatives by using benzyl oxides as raw material
  • Method of synthesizing diphenyl-methane derivatives by using benzyl oxides as raw material

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Effect test

Embodiment 1

[0024] A kind of synthetic method taking benzyl ether as the diphenylmethane derivative of raw material, its concrete steps are as follows:

[0025] (1) Take benzyl n-octyl ether as the benzylation reagent, boron trifluoride ether as the reaction reagent, and toluene as the raw material and also as the solvent. The ratio is 1:0.2:2. First add benzyl n-octyl ether (220.4mg, 1.0mmol) into the reactor, then add toluene (2.0mL), and then add boron trifluoride diethyl ether (25μL, 0.2 mmol), the addition was completed, and under open conditions, the temperature was raised to 120° C. and continued stirring for 2 hours for benzylation reaction to prepare a reaction solution of benzyltoluene.

[0026] (2) After the first (1) step is completed, the reaction solution of the benzyltoluene prepared in the (1) step is naturally cooled in the air, and the condensing system of the reactor is rinsed with dichloromethane, and the washing liquid is incorporated into the reactor in the reaction...

Embodiment 2

[0029] A kind of synthetic method using benzyl ether as a diphenylmethane derivative of raw material, its concrete steps are the same as embodiment 1, wherein:

[0030] In step (1), benzyl n-octyl ether is used as the benzylation reagent, boron trifluoride ether is the reaction reagent, and toluene is used as the raw material and also as the solvent. : The ratio of toluene to milliliter is 1:2.0:2, first add benzyl n-octyl ether (220.4mg, 1.0mmol) in the reactor, then add toluene (2.0mL), stir, then add boron trifluoride Diethyl ether (252 μL, 2.0 mmol) was added. Under open conditions, the temperature was raised to 120° C. and stirred continuously for 2 hours for benzylation reaction to prepare a benzyltoluene reaction solution.

[0031] In step (2), benzyltoluene (182 mg, yield 99%, p-:o-:m-=49:42:9) was obtained as a colorless transparent liquid.

Embodiment 3

[0033] A kind of synthetic method using benzyl ether as a diphenylmethane derivative of raw material, its concrete steps are the same as embodiment 1, wherein:

[0034] In step (1), benzyl n-octyl ether is used as the benzylation reagent, boron trifluoride ether is the reaction reagent, and toluene is used as the raw material and also as the solvent. : The ratio of toluene to milliliter is 1:1.2:2, first add benzyl n-octyl ether (220.4mg, 1.0mmol) in the reactor, then add toluene (2.0mL), and then add boron trifluoride diethyl ether under stirring (151 μL, 1.2 mmol), after the addition was completed, under open conditions, the temperature was raised to 120° C. and continued to stir for benzylation reaction for 2 hours to prepare a reaction solution of benzyltoluene.

[0035] In step (2), benzyltoluene (181 mg, yield 99%, p-:o-:m-=50:41:9) was obtained as a colorless transparent liquid.

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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 [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a synthesis method of benzylation of aromatic hydrocarbons. Background technique [0002] Diphenylmethane compounds are an important class of organic synthesis intermediates and chemical raw materials. In the synthesis of drugs and pesticides, diphenylmethane and its derivative fragments are commonly used. For example, diphenhydramine is the first antihistamine drug in human history. It is used for skin allergies, urticaria, and neurological rhinitis. It is also commonly used in preoperative sedation and psychotherapy. In industry, diphenylmethane and its derivatives can be used as aromatics, spices, polycarbonate resin monomers, dyes, etc., and the market application prospect is good. [0003] There are many ways to synthesize diphenylmethane and its derivatives, usually through Friedel-Crafts alkylation reaction, coupling reaction and reduction ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/04C07C15/16C07C2/88C07C25/18C07C17/263C07C43/205C07C41/30
Inventor 黎学明李昱熊燕杨建春凌学戈张晓慧黄若峰
Owner CHONGQING UNIV
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