Substituted benzophenone and preparation method thereof

A technology of benzophenone and benzophenones, which is applied in the field of compound synthesis, can solve the problems of harsh reaction conditions, limited application of phosgene, complicated operation, etc., and achieves the effects of simple operation and overcoming inability to be widely used

Inactive Publication Date: 2014-01-22
XI AN JIAOTONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthetic methods of benzophenones mainly include: carbon monoxide method, that is, carbon monoxide reacts with organometallic reagents under specific conditions to prepare diaryl ketones, but this method is only suitable for the preparation of symmetrical diaryl Methanone compounds, and the reaction conditions are relatively harsh, the operation is

Method used

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  • Substituted benzophenone and preparation method thereof
  • Substituted benzophenone and preparation method thereof
  • Substituted benzophenone and preparation method thereof

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preparation example Construction

[0042] see figure 1 , the preparation method of above-mentioned substituted benzophenone, comprises the following operations:

[0043] 1) The intermediate compound B is reacted with magnesium in an organic solvent to prepare a Grignard reagent, and then the intermediate compound A is subjected to an addition reaction, and the addition reactant is hydrolyzed to obtain a diphenylcarbinol compound;

[0044] The structural formula of the intermediate compound B is:

[0045]

[0046] The structural formula of the intermediate compound A is:

[0047]

[0048] 2) Oxidizing diaryl carbinol compounds to generate benzophenone compounds to obtain substituted benzophenones with substituents on the benzene rings at both ends of the carbonyl group.

[0049] Specifically, the preparation of the described diphenylcarbinol compound specifically includes the following operations:

[0050] Put anhydrous magnesium chips activated with ammonium chloride solution in a reaction vessel, add ...

Embodiment 1

[0062] Compound I: Synthesis of (5-benzyloxy-2-methoxyphenyl)(2-bromo-3,4-dimethoxyphenyl)methanone, in the structural formula of the compound R 1 , R 2 Respectively methoxy, benzyloxy, R 3 When it is hydrogen, it is prepared by the following steps:

[0063]

[0064] 1) Synthesis of compound (5-benzyloxy-2-methoxyphenyl)(2-bromo-3,4-dimethoxyphenyl)methanol

[0065] Magnesium bars (0.61 g, 0.026 mol) were treated with an aqueous solution of ammonium chloride to remove magnesium oxide from the surface of the bars. Rinse the magnesium bars with tetrahydrofuran to remove water. The treated magnesium strips are placed in a two-neck bottle, and vacuumized to make the surface of the magnesium strips dry. Add two grains of iodine, heat slightly to make it volatilize and adhere to the surface of the magnesium bar, and the magnesium bar is golden yellow. After dissolving 2-bromo-4-benzyloxyanisole (5.0g, 0.017mol) in anhydrous tetrahydrofuran, it was slowly injected into the ab...

Embodiment 2

[0069] Compound Ⅱ: Synthesis of (3-benzyloxy-2-bromo-4-methoxyphenyl)(5-benzyloxy-2-methoxyphenyl)methanone

[0070]

[0071] 1) Synthesis of (5-benzyloxy-2-methoxyphenyl)(3-benzyloxy-4-methoxyphenyl)methanone

[0072] Magnesium chips (0.62 g, 0.025 mol) were activated with saturated ammonium chloride solution until bright, filtered with suction, washed with a large amount of water first, and washed with anhydrous tetrahydrofuran immediately after changing the filter paper until anhydrous. After adding to the three-necked bottle, evacuate three times with an oil pump under heating conditions, and dry and store under a nitrogen atmosphere. After adding a grain of iodine to the system, evacuate and fill with nitrogen three times. First add a small amount of 2-bromo-4-benzyloxyanisole (5.00g, 0.017mol) in anhydrous tetrahydrofuran solution through a syringe, and initiate the reaction under heating conditions (the solution changes from light yellow to taupe), and then the rema...

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Abstract

The invention discloses substituted benzophenone and a preparation method thereof. The substituted benzophenone has a benzophenone structure, can be used as a hydrogen abstraction type photoinitiator, can be widely applied to ultraviolet light curing and other fields, and can also be used as a key intermediate to synthesize a poly-substituted fluorenone type compound. The preparation method of the substituted benzophenone, provided by the invention, is simple to operate, toxic substances are not used, an intermediate compound B and an intermediate compound A are ingeniously utilized to construct a benzhydrol structure through Grignard reaction, and the compound with the benzophenone structure is further obtained by oxidation with pyridinium chlorodichromate; the defect that synthesis methods of benzophenone type compounds in the prior art can not be widely applied is overcome.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and relates to a substituted benzophenone and a preparation method thereof. Background technique [0002] Benzophenone compounds have important physical, chemical and biological properties due to the different positions, types and quantities of substituents on the benzene rings at both ends of the carbonyl group, so they are widely used in plastics, medicine, spices and electronics industries, etc. field. With the continuous deepening of natural medicine research, a variety of specific core structure chemical components have been found to have unique pharmacological activities, among which diaryl ketones are a type of natural products with special skeleton structures, and in The distribution in natural plants is also relatively concentrated, especially in plants such as Daphne, Hypericum, Garcinia and Mango. At present, the research on its biological activity mainly focuses on anti-i...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/29C07F7/18C08F2/48
CPCC07C49/84C07C41/30C07C45/305C07F7/1804C07C43/23C07C43/315
Inventor 王嗣岑张杰贺浪冲沈秀秀胡志刚魏芬
Owner XI AN JIAOTONG UNIV
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