Method for synthesizing aromatic aldehyde, aromatic ketone and aromatic ester through catalytically oxidizing alkyl aromatic compound by iron
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A technology for aromatic compounds and alkylene oxides, which is applied in the field of catalytic synthesis, can solve the problems of poor compatibility of functional groups, high reaction costs, and low reaction efficiency, and achieve the effects of high selectivity, good reaction selectivity, and wide sources
Active Publication Date: 2017-09-29
NANJING NORMAL UNIVERSITY
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[0003] Purpose of the invention: In view of the fact that the existing synthetic methods of aromatic aldehydes, aromatic ketones and aromatic esters through the iron-catalyzed oxidation of alkyl aromatics benzylic carbon-hydrogen bonds need to use complex ligands, resulting in high reaction costs, low reaction efficiency, and poor selectivity (especially It is the problem of peroxidation and overreduction in oxidized methylbenzene compounds, which has not been solved) the amount of solvent participating in the reaction and / or the challenging problem of poor compatibility of functional groups and narrow scope of application. The present invention provides a simple and easy-to-use and Inexpensive iron catalysts, cheap and environmentally friendly oxidants, under the action of safe and stable accelerators, efficiently and selectively catalyze the oxidation of benzylic carbon-hydrogen bonds in alkylaromatics to synthesize aromatic aldehydes, aromatic ketones, and aromatic esters
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Embodiment 1
[0027] Compound 1: Add ferrous acetylacetonate (0.025mmol), polymethylhydrogensiloxane (0.75mmol), potassium persulfate (0.25mmol), 1a (0.25mmol), acetonitrile (1mL), water to a 25mL reaction flask in sequence (1 mL), the reaction mixture was reacted at 80°C for 6h. After the reaction, add ammonia water (2 mL) to remove polymethylhydrogen siloxane, add 10 mL of saturated saline, and extract with ether (10 mL×3), combine the organic phases, evaporate the solvent under reduced pressure, and separate by column chromatography to obtain a yield of 80%. .
Embodiment 2
[0029] Compound 2: Iron acetylacetonate (0.025mmol), polymethylhydrogensiloxane (0.75mmol), potassium persulfate (0.25mmol), 1b (0.25mmol), acetonitrile (1mL), water ( 1 mL), the reaction mixture was reacted at 80°C for 3h. After the reaction, add ammonia water (2 mL) to remove polymethylhydrogen siloxane, add 10 mL of saturated saline, and extract with ether (10 mL×3), combine the organic phases, evaporate the solvent under reduced pressure, and separate by column chromatography to obtain a yield of 80%. .
Embodiment 3
[0031] Compound 3: Add ferrous acetylacetonate (0.025mmol), polymethylhydrogensiloxane (0.75mmol), potassium persulfate (0.25mmol), 1c (0.25mmol), acetonitrile (1mL), water to a 25mL reaction flask in sequence (1 mL), the reaction mixture was reacted at 80° C. for 3 h. After the reaction, add ammonia water (2 mL) to remove polymethylhydrogen siloxane, add 10 mL of saturated saline, and extract with ether (10 mL×3), combine the organic phases, evaporate the solvent under reduced pressure, and separate by column chromatography to obtain a yield of 80%. .
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Abstract
The invention discloses a method for synthesizing aromatic aldehyde, aromatic ketone and aromatic ester through catalytically oxidizing an alkyl aromatic compound by iron, and belongs to the technical field of catalytic synthesis. According to the method, a low-cost and environment-friendly iron catalyst is used under a normal pressure; under the action of hydrogen and silicon reagents serving as an accelerant and an oxidant, a side chain of an aromatic hydrocarbon is oxidized into a carbonyl group for generating the corresponding aromatic aldehyde, aromatic ketone and aromatic ester. The method for preparing the aromatic aldehyde, the aromatic ketone and the aromatic ester through a catalytic oxidation reaction, which is provided by the invention, has numerous advantages that a catalyst, reaction raw materials, the oxidant and a silicon reagent are wide in sources and good in stability and is low-cost and environment-friendly; the alkyl aromatic compound is metered to participate in a reaction; the reaction condition is mild; the compatibility of functional groups is good; the scope of application is wide; the reaction selectivity is good; in an optimized reaction condition, the separation yield of a target product can be up to approximately 95 percent.
Description
technical field [0001] The invention belongs to the technical field of catalytic synthesis, and more specifically relates to a method for iron-catalyzed synthesis of aromatic aldehydes, aromatic ketones and aromatic esters. Methods for aryl aldehydes, aryl ketones and aryl esters. Background technique [0002] Aromatic aldehydes, aryl ketones and aryl esters are organic synthesis intermediates with high added value, which are widely used in the synthesis of medicines, pesticides, dyes and fragrances. Among the current methods for the synthesis of aromatic aldehydes, aromatic ketones, and aromatic esters, the liquid-phase catalytic oxidation of benzylic carbon-hydrogen reactions with alkylaromatics as substrates using iron catalysts has attracted widespread attention because of the cheap catalysts and environmental friendliness of the method; Wide, stable and cheap material sources; advantages of high atom economy and low emissions. However, there are some challenging probl...
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