A kind of synthetic method of 2-methyl-1,3-diphenylpropan-1-one

A synthesis method and diphenyl technology, which are applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of reaction efficiency and other problems, and achieve the advantages of simple operation, high reaction efficiency and shortened reaction time. Effect

Active Publication Date: 2020-07-31
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Various transition metal complexes (Ir, Rh, Ru, Pd, Cu, Os, etc.) have been developed for heterogeneous and heterogeneous BH catalysis, but there are still problems of reaction efficiency

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a 15 ml Schlenk tube, add 53.7 mg (0.4 mmol) of propiophenone, 47.6 mg (0.44 mmol) of benzyl alcohol, 26.63 mg (0.25 equiv) of potassium phosphate trihydrate, and 0.5 ml of tert-amyl alcohol, and stir magnetically under an argon atmosphere. At a temperature of 120°C, react for 12 h. After TLC analysis, No Reaction.

Embodiment 2

[0021] The synthetic method of 2-methyl-1,3-diphenylpropan-1-one of the present embodiment, the steps are as follows:

[0022] In a 15 ml Schlenk tube, add 53.7 mg (0.4 mmol) propiophenone, 47.6 mg (0.44 mmol) benzyl alcohol, 1.55 mg (0.5 mol%) pincer metal ruthenium(II) compound, 26.63 mg (0.25 equiv) trihydrate Potassium phosphate, 0.5 ml tert-amyl alcohol, magnetic stirring under argon atmosphere, and react at 120°C for 12 h. Through TLC analysis, raw material propiophenone has reacted completely. Vacuum rotary evaporation, separation and purification by thin layer chromatography, the product 2-methyl-1,3-diphenylpropan-1-one has a mass of 64.63 mg and a yield of 72%. product by 1 H NMR, 13 Confirmed by C NMR. 1 H NMR (400MHz, CDCl 3 ) δ 7.96-7.89(m, 2H), 7.53-7.49(m, 1H), 7.42(t, J = 7.6 Hz, 2H), 7.26-7.16 (m, 5H),3.78-3.69 (m, 1H), 3.16 (dd, J = 6.2 Hz, 13.8Hz,1H), 2.68 (dd, J = 7.8Hz,13.8Hz,1H), 1.19 (d, J = 7.2Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ203.8...

Embodiment 3

[0024] The synthetic method of 2-methyl-1,3-diphenylpropan-1-one of the present embodiment, the steps are as follows:

[0025] In a 15 ml Schlenk tube, add 53.7 mg (0.4 mmol) propiophenone, 43.3 mg (0.4 mmol) benzyl alcohol, 1.55 mg (0.5 mol%) pincer metal ruthenium(II) compound, 10.8 mg (0.5 equiv) sodium methoxide , 0.5 ml of a mixed solution of dichloromethane and toluene, stirred magnetically under an argon atmosphere, and reacted for 12 h at a temperature of 120 °C. Through TLC analysis, raw material propiophenone has reacted completely. Vacuum rotary evaporation, separation and purification by thin layer chromatography, the product 2-methyl-1,3-diphenylpropan-1-one was 61.01 mg, and the yield was 68%.

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Abstract

The invention discloses a 2-methyl-1,3-diphenyl propyl-1-keton synthesizing method which comprises the following steps: sequentially adding propiophenone, benzyl alcohol, a catalyst, alkali and a solvent into a reactor; magnetic stirring to react under the argon phenomenon and fully reacting in an oil bath pot. According to the 2-methyl-1,3-diphenyl propyl-1-keton synthesizing method disclosed bythe invention, alcohol is utilized as a starting material for forming C-C bonds, and the starting material has the advantages of cheapness, easiness in treating and environmental friendliness. The method disclosed by the invention avoids the problem that varieties of antioxidants are utilized in a traditional method to cause a lot of byproducts. According to the method disclosed by the invention,NNN type pincerlike metal ruthenium (II) compound is utilized as the catalyst for catalytic reaction; thus, reaction can be finished in one step, reaction time is greatly shortened, operation is convenient, a reaction efficiency is high, and a requirement of green chemical sustainable development is met.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 2-methyl-1,3-diphenylpropan-1-one. Background technique [0002] The ability to manipulate and extend carbon functionality through carbon-carbon bond-forming reactions is crucial for synthetic organic chemistry, such as medicinal chemistry, pesticides, and natural product synthesis. In this case, aldehydes and ketones play a key role because their carbonyl functionality can participate in an array of reactions leading to carbon-carbon bond formation, such as organometallic reagents (organolithium, Grignard reagents, etc.), cyanide, Attack of various carbonyl nucleophiles such as enolates derived from active methylene compounds, and preparation by Wittig-type reagents. Furthermore, these compounds can also act as C-nucleophiles via the corresponding enols, eg in aldol reactions. In recent years, the use of alcohols as starting material...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/68C07C49/784
CPCC07C45/68C07C49/784
Inventor 郝新奇王艳冰赵福杰曹筱妞杨发琉朱新举宋毛平
Owner ZHENGZHOU UNIV
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