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Allylation method of aromatic hydrocarbon

A technology for allylation and aromatic hydrocarbons, applied in the field of organic synthesis, can solve the problems of expensive catalyst, increase reaction cost, and high equipment requirements, and achieve the effects of simple structure, cost saving, and low equipment requirements

Inactive Publication Date: 2011-07-06
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] (1) The catalyst is expensive and highly toxic
[0006] (2) The conditions are harsh and the reaction time is long
[0007] (3) Allyl halides are used as allylation reagents, which are not environmentally friendly
[0008] (4) The reaction requires the use of additives, which makes the operation complicated
[0009] (5) Some reactions need to be carried out under the protection of nitrogen, which requires high equipment, cumbersome operation, and increases the reaction cost

Method used

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  • Allylation method of aromatic hydrocarbon

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] a FeCl 3 ·6H 2 O catalyzes the method for the synthetic allylation product of aromatic hydrocarbons, and its concrete steps are as follows:

[0026] (1) Toluene is used as a raw material and used as a solvent, and FeCl 3 ·6H 2 O is a catalyst, with cinnamyl acetate as an allylation reagent, according to cinnamyl acetate (mmol): FeCl 3 ·6H 2 The ratio of O (mmol):toluene (ml) is 1:0.2:50, and FeCl is first added to the reactor 3 ·6H 2 O (54.06mg, 0.1mmol) catalyst and cinnamyl acetate (176.21mg, 0.1mmol) were added, and toluene (50mL) was added. After the addition was completed, the temperature was raised to 80°C, and the reaction was carried out under stirring for 0.5 hours.

[0027] (2) After the first (1) step is completed, the allylation product reaction liquid prepared in the (1) step is 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 solution. ...

Embodiment 2

[0029] a FeCl 3 ·6H 2 O catalyzes the method for the synthetic allylation product of aromatic hydrocarbons, and its specific steps are with embodiment 1, wherein:

[0030] In step (1), take o-xylene as raw material and do solvent concurrently, use FeCl 3 ·6H 2 O is a catalyst, with cinnamyl acetate as an allylation reagent, according to cinnamyl acetate (mmol): FeCl 3 ·6H 2 The ratio of O (mmol): o-xylene (ml) is 1: 0.2: 50, FeCl is first added to the reactor 3 ·6H 2 O (54.06mg, 0.1mmol) catalyst and cinnamyl acetate (176.21mg, 0.1mmol) were added, and o-xylene (50mL) was added. After the addition was completed, the temperature was raised to 80°C, and the reaction was carried out under stirring for 0.5 hours.

[0031] In step (2), cinnamyl xylene (167.1 mg, yield 75%) was obtained as a colorless transparent liquid.

Embodiment 3

[0033] a FeCl 3 ·6H 2 O catalyzes the method for the synthetic allylation product of aromatic hydrocarbons, and its specific steps are with embodiment 1, wherein:

[0034] In step (1), take m-xylene as raw material and do solvent concurrently, use FeCl 3 ·6H 2 O is a catalyst, with cinnamyl acetate as an allylation reagent, according to cinnamyl acetate (mmol): FeCl 3 ·6H 2 The ratio of O (mmol): m-xylene (ml) is 1: 0.2: 50, FeCl is first added to the reactor 3 ·6H 2 O (54.06mg, 0.1mmol) catalyst and cinnamyl acetate (176.21mg, 0.1mmol) were added, m-xylene (50mL) was added, the temperature was raised to 80°C, and the reaction was carried out under stirring for 0.5 hours.

[0035] In step (2), cinnamyl xylene (140.5 mg, yield 63%) was obtained as a colorless transparent liquid.

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Abstract

The invention relates to an allylation method for catalyzing aromatic hydrocarbon by FeCl3. 6H2O, belonging to a synthesis method of allyl aromatic hydrocarbon. The method takes various aromatic hydrocarbons as raw material, the FeCl3. 6H2O as catalyst as well as cinnamyl acetate and cinnamyl alcohol as allylation reagent, and the finished product can be obtained by further reaction, concentration and purification, so that the allylation reaction can be realized. The allylation method has the characteristics of being simple in method, simple and convenient to operate, low in production cost, convenient to popularize and apply and the like. By the allylation of the aromatic hydrocarbon, the method leads functional group to be introduced, so that the complicated product molecule is further constructed, and the demand of synthesis pharmaceutical industry can be met.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an allylation method of aromatic hydrocarbons. Background technique [0002] Allylation reaction is an important class of organic reactions, which can directly introduce allyl groups in organic molecules. Common allylation reactions include electrophilic allylation reactions of aldehydes and ketone carbonyls, and carbonyl compounds α The nucleophilic allylation reaction between the -position carbon and allyl bromide, etc. The allylation reaction of arenes is to directly introduce an allyl group on the aryl group to make the aryl group functional, which undoubtedly plays an important role in the skeleton construction of the synthesis of complex organic compounds. For example, the drug chalcones and their analogs contain arene allylated structural units. [0003] As for the allylation process of arenes, there are already published methods. In 1997, Junko pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C2/86C07C15/50
Inventor 熊燕张舒婷张旭凌学戈
Owner CHONGQING UNIV
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