CN109534975B - Catalytic synthesis method of 2-hydroxybenzophenone compound - Google Patents
Catalytic synthesis method of 2-hydroxybenzophenone compound Download PDFInfo
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Abstract
The invention discloses a 2-hydroxybenzophenone compound and a green catalytic synthesis method thereof, wherein the 2-hydroxybenzophenone compound is obtained with high yield under the conditions that benzofuranone and a derivative raw material thereof, nickel chloride as a catalyst, toluene as a solvent, di-tert-butyl peroxide as an oxidant and sodium carbonate as alkali are used. The method has the advantages of low cost, high yield, simple and convenient operation, no pollution and the like, and has potential industrial application prospect. The method provides a cheap and green way for preparing the 2-hydroxybenzophenone compound.
Description
[ technical field ] A method for producing a semiconductor device
The invention belongs to the field of catalytic organic synthesis, and particularly relates to a high-efficiency catalytic synthesis method of a 2-hydroxybenzophenone compound.
[ background of the invention ]
The 2-hydroxybenzophenone derivative is an additive which is widely applied, can strongly absorb ultraviolet light, and is also widely applied to the fields of daily chemical industry, medicines, pesticides, plastics, coatings and the like. 2-hydroxy-4-methoxybenzophenone (UV-9) as light stabilizer. The ultraviolet light absorbing paint can effectively absorb ultraviolet light of 200-400 nm, hardly absorbs visible light, can be used for paint and various plastic products, is particularly suitable for light-colored transparent products, and is a good cosmetic additive. 2, 4-dihydroxy benzophenone is an ultraviolet absorbent and is suitable for polyvinyl chloride, polystyrene, epoxy resin, cellulose resin, unsaturated resin, paint, synthetic rubber and the like. And can be used as raw material for synthesizing other ultraviolet absorbent.
The synthesis method of the 2-hydroxybenzophenone compound can be divided into the following raw materials according to the initial raw materials: (1) taking an o-hydroxybenzaldehyde compound as a starting material; (2) benzophenone and derivatives thereof are taken as starting materials; (3) using benzoylformic acid as starting material. The 2-hydroxybenzophenone compound synthesized by taking the benzofuranone as the initial raw material has the advantages of easily obtained raw materials, simple operation, mild reaction conditions, high product yield and purity and the like, and the synthetic process reports are few. At present, the conditions for industrially producing the benzofuranone compounds are harsh, the operation is complex and the efficiency is not high, so the improved process is provided. The 2-hydroxybenzophenone compound is synthesized by using benzofuranone as an initial raw material, nickel chloride as a catalyst, di-tert-butyl peroxide as an oxidant and sodium carbonate as an alkali in an air one-pot method. At present, the method has no published documents and patent applications about synthesizing 2-hydroxybenzophenone compounds by using benzofuranone as a starting material, nickel chloride as a catalyst, di-tert-butyl peroxide as an oxidant and an air one-pot method at home and abroad.
[ summary of the invention ]
The invention aims to provide a method for efficiently synthesizing 2-hydroxybenzophenone compounds by using nickel chloride as a catalyst, di-tert-butyl peroxide as an oxidant, sodium carbonate as alkali and benzofuranone as a raw material. The method has the advantages of low cost, high yield, simple and convenient operation, no pollution and the like, and has certain feasibility for realizing the industrial production. In order to achieve the above purpose, the invention provides the following technical scheme:
in order to achieve the above purpose, the invention provides the following technical scheme:
a synthetic method of 2-hydroxybenzophenone compounds I, wherein the structural formula of the 2-hydroxybenzophenone compounds I is as follows:
wherein said R1-R2Is selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxy, phenyl, fluorine, chlorine, bromine; the green catalytic synthesis method of the compound I is characterized in that nickel chloride is used as a catalyst, benzofuranone II is used as a reaction raw material, the reaction is effectively carried out at 80 ℃ under the air condition, and the reaction is carried out for 12 hours2-hydroxybenzophenone compounds I with higher yield can be obtained within a certain time;
in the synthesis method, the structural formula of the benzofuranone and the derivative II thereof is as follows:
wherein said R1-R2Is selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxy, phenyl, fluorine, chlorine, bromine;
in the synthesis method, the dosage of the catalyst is 10 mol%; the amount of oxidant used is two equivalents; the amount of base used is two equivalents; the solvent is toluene; reacting under air; the reaction time is 12h, and the reaction temperature is 80 ℃.
The high-efficiency catalytic synthesis method of 2-hydroxybenzophenone compounds provided by the invention opens up a new low-cost 'green' approach, and has the advantages that: the benzofuranone derivative used as the raw material has wider source, higher selectivity and yield of the target product, mild reaction condition and simple and convenient reaction operation.
[ description of the drawings ]
The attached figure shows a route chart for preparing the 2-hydroxybenzophenone compound provided by the invention.
[ detailed description ] embodiments
The invention provides a high-efficiency catalytic synthesis method of 2-hydroxybenzophenone compounds, which is shown in the attached drawings: the benzofuranone derivative, a catalyst nickel chloride, an oxidant di-tert-butyl peroxide and a solvent toluene are placed in a reaction vessel and react for 12 hours in an air environment of 80 ℃, and a target product is obtained by column separation after the reaction is finished.
The invention is further illustrated below with reference to specific preparation examples:
preparation example 1
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R24-methyl) 0.02mmol, 10 mol% of nickel chloride catalyst was added0.04mmol of di-tert-butyl peroxide oxidant, 1ml of solvent toluene, 0.04mmol of sodium carbonate and reaction for 12 hours at 80 ℃ in air. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R24-methyl) to give a yellow liquid in 99% yield.
Preparation example 2
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R2H)0.02mmol, 10 mol% of nickel chloride catalyst, 0.04mmol of di-tert-butylperoxide oxidant, 1ml of toluene as a solvent, 0.04mmol of sodium carbonate, and reaction at 80 ℃ under air for 12 hours. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R2H) to yield a yellow liquid in 99% yield.
Preparation example 3
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R22-methyl) was added thereto, and the mixture was reacted for 12 hours at 80 ℃ under air with the addition of 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-t-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R22-methyl) to give a yellow liquid in 89% yield.
Preparation example 4
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R24-ethyl) was added thereto, and the mixture was reacted for 12 hours at 80 ℃ under air with the addition of 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-t-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R24-ethyl) to give a yellow liquid in 94% yield.
Preparation example 5
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R24-isopropyl), 10 mol% of nickel chloride catalyst, 0.04mmol of di-tert-butyl peroxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene solvent, and air reaction at 80 ℃ for 12 h. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R24-isopropyl) to give a yellow liquid in 99% yield.
Preparation example 6
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R24-tert-butyl) was added thereto, and the mixture was reacted for 12 hours with 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-tert-butylperoxide as an oxidizing agent, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent and air at 80 ℃. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R24-tert-butyl) to give a yellow liquid in 99% yield.
Preparation example 7
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R23, 5-dimethyl) was added thereto, and the mixture was reacted for 12 hours at 80 ℃ under air with the addition of 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-t-butylperoxide as an oxidizing agent, 0.04mmol of sodium carbonate, and 1ml of toluene as a solvent. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R23, 5-dimethyl) to give a white solid in 42% yield.
Preparation example 8
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R24-methoxy group), 10 mol% of nickel chloride catalyst, 0.04mmol of di-tert-butyl peroxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent, and air at 80 ℃ for 12 hours. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R24-methoxy) to give a yellow liquid in 82% yield.
Preparation example 9
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R24-phenyl) was added thereto, and the mixture was reacted for 12 hours at 80 ℃ under air with the addition of 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-t-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R24-phenyl) to yield a yellow liquid in 78% yield.
Preparation example 10
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R24-Cl), 10 mol% of nickel chloride catalyst, 0.04mmol of di-tert-butyl peroxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene solvent, and air reaction at 80 ℃ for 12 h. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R24-Cl) to give a yellow solid in 73% yield.
Preparation example 11
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R24-F), 10 mol% of nickel chloride catalyst, 0.04mmol of di-tert-butyl peroxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene solvent, and air reaction at 80 ℃ for 12 h. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R24-F) to yield a yellow liquid in 83% yield.
Preparation example 12
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R23-t-butyl) was added thereto, and the mixture was reacted for 12 hours with 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-t-butylperoxide oxidizing agent, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent and air at 80 ℃. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R2＝3-T-butyl) to give a yellow liquid in 99% yield.
Preparation example 13
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝H，R2O-tert-butyl) was added to the reaction mixture, and then 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-tert-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent, and the mixture was reacted at 80 ℃ under air for 12 hours. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝H，R2T-butyl o) to give a yellow liquid in 92% yield.
Preparation example 14
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝4-Cl，R2H) was added to 0.02mmol, 10 mol% of a nickel chloride catalyst, 0.04mmol of di-t-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent, and reacted at 80 ℃ under air for 12 hours. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝4-Cl，R23-tert-butyl) to give a yellow liquid in 80% yield.
Preparation example 15
The benzofuranone derivative (R) was added to a 25mL reaction tube1＝4-Br，R2H) was added to 0.02mmol, 10 mol% of a nickel chloride catalyst, 0.04mmol of di-t-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent, and reacted at 80 ℃ under air for 12 hours. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation1＝4-Cl，R23-tert-butyl) to give a yellow liquid in 98% yield.
Preparation example 16
The benzofuranone derivative (R) was added to a 25mL reaction tube12, 4-di-tert-butyl, R22, 3-dimethyl), adding nickel chloride catalyst 10 mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, reacting at 80 deg.C under airAnd (4) 12 h. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation12, 4-di-tert-butyl, R22, 3-dimethyl) to give a yellow solid in 80% yield.
Preparation example 17
The benzofuranone derivative (R) was added to a 25mL reaction tube12-methyl, R24-bromo) was added to the reaction solution, and 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-tert-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent, and the mixture was reacted at 80 ℃ under air for 12 hours. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation12-methyl, R24-bromo) to give a yellow solid in 99% yield.
Preparation example 18
The benzofuranone derivative (R) was added to a 25mL reaction tube12, 4-dimethyl, R24-bromo) was added to the reaction solution, and 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-tert-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent, and the mixture was reacted at 80 ℃ under air for 12 hours. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation12, 4-dimethyl, R24-bromo) to give a yellow solid in 30% yield.
Preparation example 19
The benzofuranone derivative (R) was added to a 25mL reaction tube12-methyl, R22-chloro) was added to the reaction solution, and then 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-t-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent, and the mixture was reacted at 80 ℃ for 12 hours under air. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation12-methyl, R22-chloro) to give a yellow solid in 71% yield.
Preparation example 20
The benzofuranone derivative (R) was added to a 25mL reaction tube12-methyl, R24-chloro) was added thereto, and the mixture was reacted for 12 hours at 80 ℃ under air with the addition of 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-t-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation12-methyl, R24-chloro) to give a yellow solid in 99% yield.
Preparation example 21
The benzofuranone derivative (R) was added to a 25mL reaction tube14-tert-butyl, R24-chloro) was added thereto, and the mixture was reacted for 12 hours at 80 ℃ under air with the addition of 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-t-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation14-tert-butyl, R24-chloro) to give a yellow solid in 99% yield.
Preparation example 22
The benzofuranone derivative (R) was added to a 25mL reaction tube14-tert-butyl, R22-chloro) was added to the reaction solution, and then 10 mol% of a nickel chloride catalyst, 0.04mmol of a di-t-butylperoxide oxidant, 0.04mmol of sodium carbonate, 1ml of toluene as a solvent, and the mixture was reacted at 80 ℃ for 12 hours under air. After the reaction is finished, the target compound 2-hydroxybenzophenone compound (R) is obtained by column chromatography separation14-tert-butyl, R22-chloro) to give a yellow solid in 90% yield.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent should be defined by the appended claims.
Claims (2)
1. A synthetic method of 2-hydroxybenzophenone compounds I is disclosed, wherein the structural formula of the 2-hydroxybenzophenone compounds I is as follows:
wherein R is1-R2Selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxy, phenyl, fluoro, chloro, bromo; it is characterized in that; taking benzofuranone II as a reaction raw material, nickel chloride as a catalyst, di-tert-butyl peroxide as an oxidant, sodium carbonate as an alkali and toluene as a solvent, and effectively reacting at 80 ℃ in the air for 12 hours to obtain a 2-hydroxybenzophenone compound I; the structural formula of the benzofuranone II is as follows:
2. the method for synthesizing 2-hydroxybenzophenone compound I according to claim 1, wherein the catalyst is used in an amount of 10 mol%; the amount of oxidant used is two equivalents; the amount of base used is two equivalents.
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