CN118666659A - Benzoin based on benzimidazole bromide catalysis and synthesis method of benzoin derivative - Google Patents

Benzoin based on benzimidazole bromide catalysis and synthesis method of benzoin derivative Download PDF

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CN118666659A
CN118666659A CN202410746959.3A CN202410746959A CN118666659A CN 118666659 A CN118666659 A CN 118666659A CN 202410746959 A CN202410746959 A CN 202410746959A CN 118666659 A CN118666659 A CN 118666659A
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benzoin
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邹慧
李伟
马芊芊
阮班锋
岳妍妍
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Hefei University
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Hefei University
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Abstract

The invention discloses a benzoin and a synthesis method of a benzoin derivative based on benzimidazole bromine salt catalysis, and relates to the technical field of organic synthesis.A benzoin and a benzoin derivative are synthesized by a one-pot reaction in the presence of a catalyst and alkali by taking benzaldehyde or substituted benzaldehyde as a reaction raw material and water as a reaction solvent; the catalyst adopted by the invention is easy to obtain and has small dosage, the preparation cost of benzoin and derivatives thereof can be reduced, and the catalyst is not required to be recycled after the reaction is finished, and the filtrate can be directly reused, so that the operation steps are simplified; and water is used as a reaction solvent, so that the method is safe and environment-friendly, and the solvent input cost can be reduced.

Description

Benzoin based on benzimidazole bromide catalysis and synthesis method of benzoin derivative
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a synthesis method of benzoin and derivatives thereof based on benzimidazole bromine salt catalysis.
Background
Benzoin and its derivatives are a very important class of chemical structures, ubiquitous in a variety of bioactive molecules, synthetic drugs, and natural products, and are key intermediates for the preparation of some advanced materials and other important compounds. Benzoin ether obtained by oxidation of benzoin ketone and benzoin ether obtained by re-ether formation and benzoin ester derivative obtained by acylation have wide application in photosensitizers of ultraviolet curing resins and microporous organic polymeric materials.
Benzoin (Benzonum)
Benzonum and its derivatives are prepared mainly by the benzoin condensation reaction (benzoin condensation). The classical benzoin synthesis uses sodium cyanide or potassium cyanide as a catalyst, and the yield is high, but the toxicity of the synthesized product is high, so that the environment is easy to pollute and the health of a human body is damaged.
In 1943, ukai and the like find that vitamin B 1 can also catalyze benzoin condensation reaction of benzaldehyde, high-concentration cyanide is avoided being used as a catalyst of the reaction, and toxicity of the reaction is greatly reduced. However, the synthesis process catalyzed by vitamin B 1 has the problems of complicated operation, high time and energy consumption, poor process reproducibility and low yield. Subsequently, chemists have found that vitamin B 1 is a thiazole salt compound through intensive studies. Breslow in 1958 proposed a catalytic mechanism for the reaction involving vitamin B 1. Thus various nitrogen heterocyclic carbene precursors, such as thiazole salts, triazole salts, imidazole salts, and the like, are used to catalyze benzoin reactions. However, the reaction systems mostly use organic reagents as solvents, the reaction time is long, and the synthesis of some catalysts is complex, the dosage is large, so that the industrial production is not facilitated. For example: in the method disclosed in CN109665953A, nitrogen protection is required for the reaction, and the catalyst synthesis is complex; in the method disclosed in CN104003863A, a large amount of phosphate solution is needed for reaction, and the method is not suitable for industrial production; in the method disclosed in CN113548950B, ultrasonic assistance is needed, which is not beneficial to industrial production. Therefore, the exploration of a simpler, safer, faster and cheaper green chemical synthesis method for synthesizing benzoin and derivatives thereof is still of great significance.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a synthesis method of benzoin and derivatives thereof, which uses benzimidazole bromide as a catalyst and water as a reaction solvent, so that the process environment friendliness is improved, the reaction time is shortened, and the yield of a target product is increased.
The invention aims to provide a benzoin and a synthesis method of a benzoin derivative based on benzimidazole bromine salt catalysis, which is characterized in that benzaldehyde or substituted benzaldehyde is used as a reaction raw material, water is used as a reaction solvent, and benzoin and a benzoin derivative are synthesized through one-pot reaction in the presence of a catalyst and alkali.
In a further technical scheme, the catalyst is one or more of 1-methyl-3-butyl benzimidazole bromide, 1-methyl-3-octyl benzimidazole bromide and 1-methyl-3-dodecyl benzimidazole bromide, preferably 1-methyl-3-butyl benzimidazole bromide.
In a further technical scheme, the dosage of the catalyst is 0.01-0.1 times of the molar quantity of benzaldehyde or substituted benzaldehyde. The catalyst dosage is controlled, and the catalyst cost is controlled while the reaction is ensured to be complete.
In a further technical scheme, the substituted benzaldehyde is one or more substituted benzaldehydes selected from alkyl, alkoxy, halogen, hydroxyl, amino, nitro, cyano and amido. Of course, other substituents common in the art are also included, provided that the substituent does not interfere with the progress of the benzoin condensation reaction.
In a further embodiment, the base is an inorganic base or an organic base. Compared with organic alkali, the inorganic alkali has low price, and can control the production cost while ensuring the complete reaction. Meanwhile, the concentration of alkali needs to be controlled, so that the corrosion to the reactor is reduced.
In a further technical scheme, the inorganic base is selected from one or more of sodium hydroxide, potassium carbonate and sodium carbonate; the organic base is selected from one or more of triethylamine, diisopropylethylamine and 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU).
In a further embodiment, the temperature of the one-pot reaction is 30-80 ℃, preferably 30-40 ℃.
In a further embodiment, the one-pot reaction takes from 1 to 24 hours, preferably from 2 to 12 hours. Advantages of the one-pot method include reduced solvent and energy waste, simplified production process, reduced production cost, etc.
The beneficial effects of the invention are as follows:
(1) The catalyst adopted by the invention is easy to obtain and has small dosage, the preparation cost of benzoin and derivatives thereof can be reduced, and the catalyst is not required to be recycled after the reaction is finished, and the filtrate can be directly reused, so that the operation steps are simplified.
(2) The invention takes water as the reaction solvent, which is safe and environment-friendly and can reduce the solvent input cost.
(3) The synthesis method of benzoin and the derivatives thereof provided by the invention can be carried out at a lower reaction temperature, the reaction energy consumption is low, and the production cost can be greatly reduced.
Drawings
FIG. 1 is a hydrogen spectrum of benzoin;
FIG. 2 is a carbon spectrum of benzoin;
FIG. 3 is a hydrogen spectrum of 1-methyl-3-butylbenzimidazole bromide;
FIG. 4 is a hydrogen spectrum of 1-methyl-3-octylbenzimidazole bromide;
FIG. 5 is a hydrogen spectrum of 1-methyl-3-isopropylimidazole bromide;
FIG. 6 is a hydrogen spectrum of 1-methyl-3-dodecylbenzimidazole bromide;
FIG. 7 is a hydrogen spectrum of 4' -methyl-2-hydroxyacetophenone;
FIG. 8 is a hydrogen spectrum of 4' -fluoro-2-hydroxyacetophenone;
FIG. 9 is a hydrogen spectrum of 4' -methoxy-2-hydroxyacetophenone.
Detailed Description
The invention is further described below with reference to specific embodiments and illustrations in order to make the technical means, the creation features, the achievement of the purpose and the effect of the implementation of the invention easy to understand.
Example 1: synthesis of catalyst
Example 1-1
N-methyl benzimidazole (7.5 mmol), bromo-N-butane (8.3 mmol) and 10mL acetonitrile are sequentially added into a 50mL round bottom flask, the mixture is heated and refluxed for 24h, cooled to room temperature, white solid is separated out, suction filtration is carried out, filter cakes are washed by ethyl acetate (10 mL multiplied by 3), and 1.2g of 1-methyl-3-butyl benzimidazole bromide is obtained after drying, the yield is 83％.1HNMR(CDCl3,400MHz)δ:10.95(s,1H),7.59～7.79(m,4H),4.54～4.60(m,2H),4.28(s,3H),1.95～2.02(m,2H),1.38～1.44(m,2H),0.94(t,J＝8Hz,3H);13CNMR(CDCl3,400MHz)δ:142.7,132.1,131.1,127.2,112.5,47.5,35.6,31.3,18.7,12.5;FT-IR(neat)ν:3198.7,3145.5,3002.7,2981.2,2933.2,1813.9,1619.8,1573.0,1459.9,1358.7,1255.1,1131.8,1009.3,775.8cm－1.ESI-HR-MS C12H17N2m/z:189.1389[M-Br]+.
Examples 1 to 2
The synthesis was the same as that of example 1-1 except that n-bromobutane was replaced with n-bromooctane to give 1.5g of 1-methyl-3-octylbenzimidazole bromide in the yield of 62％.1HNMR(CDCl3,400MHz),δ:11.09(s,1H),7.62～7.79(m,4H),4.57(t,J＝8Hz,2H),4.28(s,3H),2.40～2.48(m,2H),1.22～1.43(m,12H),0.82(t,J＝8Hz,3H);13CNMR(CDCl3,400MHz),δ:141.7,134.1,130.6,126.0,110.7,54.3,35.4,31.6,29.5,28.9,27.0,22.5,14.5;FT-IR(neat)ν:3477.3,3048.6,3041.8,2921.1,2858.0,1818.8,1519.1,1484.3,1432.0,1354.9,1218.2,1139.5,1009.3,872.3,784.8cm－1.ESI-HR-MS C16H25N2m/z:245.2019[M-Br]+.
Examples 1 to 3
The synthesis was the same as in example 1-1 except that bromo-n-butane was replaced with bromo-n-dodecane to give 2.25g of 1-methyl-3-dodecylbenzimidazole bromide in the yield of 79％.1HNMR(CDCl3,400MHz)δ:11.22(s,1H),7.64～7.77(m,4H),4.57～4.60(m,2H,),4.29(s,3H),2.19～2.33(m,2H),1.23～1.45(m,18H),0.86(t,J＝8Hz,3H);13CNMR(CDCl3,400MHz),δ:142.4,131.6,130.6,126.8,110.7,47.7,32.9,31.8,28.4,24.6,23.1,22.5,14.8;FT-IR(neat)ν:3485.3,3059.0,2918.4,2849.9,1820.8,1589.9,1487.5,1379.4,1217.5,1022.7,874.5,788.1,749.58cm－1.ESI-HR-MS C20H33N2m/z:301.2646[M-Br]+.
Comparative example 1: synthesis of 1-methyl-3-isobutyl benzimidazole bromide
The synthesis was the same as in example 1 except that bromoisobutane was substituted for bromoisobutane to give 0.4g of 1-methyl-3-isobutylbenzimidazole bromide in the yield of 22％.1HNMR(D2O,400MHz)δ:9.18(s,1H),7.55～7.82(m,2H),7.53～7.55(m,2H),4.84～4.93(m,1H),3.95(s,3H),1.54(d,J＝4Hz,6H);13CNMR(D2O,400MHz),δ:139.5,132.3,130.7,126.7,126.5,113.3,112.8,50.8,32.7,21.1.ESI-HR-MS C11H15N2m/z:175.1233[M-Br]+.
Example 2: synthesis of Benzonum
Example 2-1
To a 10mL reaction flask were added 1-methyl-3-butylbenzimidazole bromide (1 mmol), benzaldehyde (10 mmol), naOH (2 mmol) and 10mL of water, and the mixture was heated to 30℃in a water bath and stirred for reaction for 1h. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 78%.
Example 2-2
To a10 mL reaction flask were added 1-methyl-3-dodecylbenzimidazole bromide (1 mmol), benzaldehyde (10 mmol), naOH (2 mmol) and 2mL of water, and the mixture was heated to 30℃in a water bath and stirred for reaction for 1h. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 72%.
Examples 2 to 3
To a 10mL reaction flask were added 1-methyl-3-octylbenzimidazole bromide (1 mmol), benzaldehyde (2 mmol), naOH (2 mmol) and 2mL of water, and the mixture was heated to 30℃in a water bath and stirred for reaction for 1h. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 76%.
Examples 2 to 4
To a 10mL reaction flask were added 1-methyl-3-butylbenzimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), triethylamine (2 mmol) and 2mL of water, and the mixture was heated to 30℃in a water bath and stirred for reaction for 1h. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 51%.
Examples 2 to 5
To a 10mL reaction flask was added 1-methyl-3-butylbenzimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), DBU (2 mmol) and water 2mL, and the mixture was heated to 30℃in a water bath and stirred for reaction for 1h. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 76%.
Examples 2 to 6
To a 10mL reaction flask, 1-methyl-3-butylbenzimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), 1mL of 5% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 30℃in a water bath and stirred for reaction for 1h. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 77%.
Examples 2 to 7
To a 10mL reaction flask, 1-methyl-3-butylbenzimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), 1mL of 10% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 30℃in a water bath and stirred for reaction for 14h. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 60%.
Examples 2 to 8
To a 10mL reaction flask, 1-methyl-3-butylbenzimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), 1mL of 20% strength by mass aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 30℃in a water bath and stirred for reaction for 14h. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 49%.
Examples 2 to 9
To a 10mL reaction flask, 1-methyl-3-butylbenzimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), 1mL of a 1% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 30℃in a water bath and stirred for reaction for 14h. After the reaction solution is cooled to room temperature, light yellow solid is obtained by filtration, and benzoin is obtained by washing and drying a filter cake. The yield was 20%.
Examples 2 to 10
To a 10mL reaction flask, 1-methyl-3-butylbenzimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), 2mL of an aqueous NaOH solution with a mass fraction of 1.6% and 2mL of water were added, and the mixture was heated to 30℃in a water bath and stirred for reaction for 14h. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 81%.
Examples 2 to 11
To a 10mL reaction flask, 1-methyl-3-butylbenzimidazole bromide (0.2 mmol), benzaldehyde (2 mmol), 1mL of a 1.6% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 30℃in a water bath and stirred for reaction for 14h. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield thereof was found to be 83%.
Examples 2 to 12
To a 10mL reaction flask, 1-methyl-3-butylbenzimidazole bromide (0.1 mmol), benzaldehyde (2 mmol), 1mL of a 1.6% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 30℃in a water bath and stirred for reaction for 14h. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 85%.
Examples 2 to 13
To a 10mL reaction flask, 1-methyl 3-butylbenzimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), 1mL of a 1.6% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 40℃in a water bath and stirred for 4 hours. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 84%.
Examples 2 to 14
To a 10mL reaction flask, 1-methyl 3-butylbenzimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), 1mL of a 1.6% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 40℃in a water bath and stirred for 2 hours. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 79%.
Examples 2 to 15
To a 10mL reaction flask, 1-methyl 3-butylbenzimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), 1mL of a 1.6% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 60℃in a water bath and stirred for 2 hours. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 76%.
Examples 2 to 16
To a 10mL reaction flask, 1-methyl 3-butylbenzimidazole bromide (0.02 mmol), benzaldehyde (2 mmol), 1mL of a 1.6% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 40℃in a water bath and stirred for reaction for 8 hours. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield was 53%.
Comparative example 2
To a10 mL reaction flask were added 1-methyl 3-isobutylbenzimidazole bromide (1 mmol), benzaldehyde (10 mmol), naOH (2 mmol) and 10mL of water, and the mixture was reacted for 1h under magnetic stirring in a water bath at 30 ℃. TLC detection showed almost no benzoin formation. From this, it was found that 1-methyl 3-isobutylbenzimidazole bromide was not suitable as a catalyst for synthesizing benzoin from benzaldehyde.
Comparative example 3
VB 1 (0.05 mmol), benzaldehyde (2 mmol), 1mL of 1.6% aqueous NaOH solution and 2mL of water were added to a 10mL reaction flask, and the mixture was heated to 40℃in a water bath and reacted for 4 hours with stirring, with almost no benzoin formation. From this, VB 1 was not suitable as a catalyst for synthesizing benzoin from benzaldehyde.
Comparative example 4
To a 10mL reaction flask, 1-methyl-3-butylimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), 1mL of a 1.6% aqueous sodium hydroxide solution and 2mL of water were added, and the mixture was heated to 40℃in a water bath and stirred for reaction for 4 hours with almost no benzoin formation. From this, it was found that 1-methyl-3-butylimidazole bromide was not suitable as a catalyst for synthesizing benzoin from benzaldehyde.
Example 3: synthesis of benzoin derivatives
Example 3-1
To a 10mL reaction flask, 1-methyl 3-butylbenzimidazole bromide (0.05 mmol), 4-fluorobenzaldehyde (2 mmol), 1mL of 1.6% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 40℃in a water bath and stirred for reaction for 8 hours. The reaction solution is cooled to room temperature, filtered, and the filter cake is washed with water and dried to obtain pale yellow solid with the yield of 68％.1HNMR(CDCl3,400MHz)δ:7.93-7.99(m,2H),7.33-7.35(m,2H),7.01-7.24(m,4H),5.92(s,1H).
Example 3-2
To a 10mL reaction flask, 1-methyl 3-butylbenzimidazole bromide (0.05 mmol), 4-chlorobenzaldehyde (2 mmol), 1mL of 1.6% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 40℃in a water bath and stirred for reaction for 8 hours. The reaction solution is cooled to room temperature, filtered, and the filter cake is washed with water and dried to obtain pale yellow solid with the yield of 73％.1HNMR(CDCl3,400MHz)δ:7.84-7.86(m,2H),7.40-7.42(m,2H),7.32-7.49(m,4H),5.90(s,1H).
Examples 3 to 3
To a 10mL reaction flask, 1-methyl 3-butylbenzimidazole bromide (0.05 mmol), 4-methylbenzaldehyde (2 mmol), 1mL of 1.6% NaOH aqueous solution and 2mL of water were added, and the mixture was heated to 40℃in a water bath and stirred for reaction for 8 hours. The reaction solution is cooled to room temperature, filtered, and the filter cake is washed with water and dried to obtain white solid with the yield of 48％.1HNMR(CDCl3,400MHz),δ:7.83-7.85(m,2H),7.20-7.24(m,4H),7.13-7.15(m,2H),5.91(s,1H),2.31(s,3H),2.37(s,3H).
Examples 3 to 4
To a 10mL reaction flask, 1-methyl 3-butylbenzimidazole bromide (0.05 mmol), 4-methoxybenzaldehyde (2 mmol), 1mL of 1.6% NaOH aqueous solution and 2mL of water were added, and the mixture was heated to 40℃in a water bath and stirred for reaction for 8 hours. The reaction solution is cooled to room temperature, filtered, and the filter cake is washed with water and dried to obtain white solid with the yield of 75％.1HNMR(CDCl3,400MHz),δ:7.90-7.94(m,2H),7.25-7.28(m,2H),6.85-6.90(m,4H),5.87(s,1H),3.84(s,3H),3.78(s,3H).
Example 4: catalyst recovery and utilization
Example 4-1
To a 10mL reaction flask, 1-methyl 3-butylbenzimidazole bromide (0.05 mmol), benzaldehyde (2 mmol), 1mL of a 1.6% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 40℃in a water bath and stirred for 4 hours. The reaction solution is cooled to room temperature, filtered, the filter cake is washed with water, the filtrate is evaporated to dryness, benzaldehyde (2 mmol) and 3mL of water are added again, the mixture is heated to 40 ℃ in water bath and stirred for reaction for 4 hours, the reaction solution is cooled to room temperature, filtered, the filter cake is washed with water, and the benzoin is obtained after drying. The yield per cycle was 45%.
Example 4-2
To a 10mL reaction flask, 1-methyl 3-butylbenzimidazole bromide (0.1 mmol), benzaldehyde (2 mmol), 1mL of a 1.6% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 40℃in a water bath and stirred for reaction for 4 hours. The reaction mixture was cooled to room temperature, filtered, the filter cake was washed with water, the filtrate was evaporated to dryness, benzaldehyde (2 mmol) and 3mL of water were added again, and the mixture was heated to 40℃in a water bath and stirred for reaction for 4 hours. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield per cycle was 81%. The yield for cycle two was 38%.
Examples 4 to 3
To a 10mL reaction flask, 1-methyl 3-butylbenzimidazole bromide (0.2 mmol), benzaldehyde (2 mmol), 1mL of 1.6% aqueous NaOH solution and 2mL of water were added, and the mixture was heated to 40℃in a water bath and stirred for reaction for 4 hours. The reaction mixture was cooled to room temperature, filtered, the filter cake was washed with water, the filtrate was evaporated to dryness, benzaldehyde (2 mmol) and 3mL of water were added again, and the mixture was heated to 40℃in a water bath and stirred for reaction for 4 hours. And (3) cooling the reaction solution to room temperature, filtering, washing a filter cake with water, and drying to obtain benzoin. The yield per cycle was 81%. The yield of four cycles was 60%.
The foregoing has shown and described the basic principles and main features of the present invention and the advantages of the present invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that the above embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made without departing from the spirit and scope of the invention, which is defined in the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.

Claims (10)

1. A synthesis method of benzoin and derivatives thereof based on benzimidazole bromide catalysis is characterized by comprising the following steps: benzaldehyde or substituted benzaldehyde is used as a reaction raw material, water is used as a reaction solvent, and benzoin and derivatives thereof are synthesized through a one-pot reaction in the presence of a catalyst and alkali.
2. The synthesis method according to claim 1, wherein: the catalyst is one or more of 1-methyl-3-butyl benzimidazole bromide, 1-methyl-3-octyl benzimidazole bromide and 1-methyl-3-dodecyl benzimidazole bromide.
3. The synthesis method according to claim 2, characterized in that: the catalyst is 1-methyl-3-butyl benzimidazole bromide.
4. The synthesis method according to claim 1, wherein: the dosage of the catalyst is 0.01-0.1 times of the molar quantity of benzaldehyde or substituted benzaldehyde.
5. The synthesis method according to claim 1, wherein: the substituted benzaldehyde is one or more of alkyl, alkoxy, halogen, hydroxyl, amino, nitro, cyano and amido.
6. The synthesis method according to claim 1, wherein: the alkali is inorganic alkali or organic alkali.
7. The method of synthesis according to claim 6, wherein: the inorganic base is selected from one or more of sodium hydroxide, potassium carbonate and sodium carbonate.
8. The method of synthesis according to claim 6, wherein: the organic base is one or more selected from triethylamine, diisopropylethylamine and DBU.
9. The synthesis method according to claim 1, wherein: the temperature of the one-pot reaction is 30-80 ℃ and the time is 1-24h.
10. The method of synthesis according to claim 9, wherein: the temperature of the one-pot reaction is 30-40 ℃ and the time is 2-12h.
CN202410746959.3A 2024-06-11 2024-06-11 Benzoin based on benzimidazole bromide catalysis and synthesis method of benzoin derivative Pending CN118666659A (en)

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