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Catalyst for synthesizing replacement ketone compounds and preparation method

A catalyst and compound technology, applied in the preparation of organic compounds, the preparation of carbon-based compounds, organic compounds/hydrides/coordination complex catalysts, etc. Wide scene, good catalytic effect

Active Publication Date: 2020-11-24
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The prior art has not disclosed a recoverable pyrazoline phosphorus iridium-containing catalyst for the synthesis of substituted ketones

Method used

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  • Catalyst for synthesizing replacement ketone compounds and preparation method
  • Catalyst for synthesizing replacement ketone compounds and preparation method
  • Catalyst for synthesizing replacement ketone compounds and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of the iridium catalyst of nitrogen-containing phosphine ligand

[0039](1) Synthesis of 1a: At 0°C, 1 g of N-Boc-O-(isopropylideneacetonesulfonyl) hydroxylamine was placed in a 100 mL round bottom flask, and 10 mL of CF 3 COOH, the reaction was stirred at 0°C for 1 h; after the reaction was completed, ice water was slowly added to the mixture, and stirred again for 15 min, filtered with suction, the filter cake was collected, and washed with distilled water several times until pH = 7, and a colorless solid was obtained as the product 1a;

[0040] (2) Synthesis of 1b: 8mmol of 2-pyridineacetonitrile was dissolved in 20mL of dichloromethane, 12mmol of 1a was dissolved in 30mL of dichloromethane, and the dichloromethane of 1a was added dropwise to the 2-pyridineacetonitrile in dichloromethane solution. Chloromethane solution, react at room temperature for 1 hour after the dropwise addition, suction filter after the reaction, collect the filter...

Embodiment 2

[0046] Example 2: Catalyzing the reaction of benzyl alcohol and acetophenone to synthesize substituted ketones

[0047] Put 1mmol of benzyl alcohol and 1.1mmol of acetophenone into a 25mL reaction flask, then add 0.1mmol of the catalyst prepared in Example 1 and 0.05mmol of NaOH, use toluene as the reaction solvent, and place it in an oil bath at 120°C for 12h with magnetic force stirring After the reaction was completed and cooled to room temperature, distilled water was added, and extracted three times with ethyl acetate, the organic phase was collected, and the organic phase was rotary evaporated to dryness, and finally separated by column chromatography to obtain the product 1,3-diphenylpropane-1 - Ketone, the reaction yield was 88% by chromatographic analysis.

Embodiment 3

[0048] Example 3: Catalyzing the reaction of benzyl alcohol and 4-methoxyacetophenone to synthesize substituted ketones

[0049] Put 1mmol of benzyl alcohol and 1.1mmol of 4-methoxyacetophenone into a 25mL reaction flask, then add 0.1mmol of the catalyst prepared in Example 1 and 0.05mmol of NaOH, use toluene as the reaction solvent, and place in 120°C oil Magnetically stirred in the bath for 12 hours, after the reaction was completed and cooled to room temperature, distilled water was added, and extracted 3 times with ethyl acetate, the organic phase was collected, and the organic phase was rotary evaporated to dryness, and finally the product 1-(4 -Methoxyphenyl)-3-phenylpropan-1-one, the reaction yield was 89% by chromatographic analysis.

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Abstract

The invention discloses a catalyst for synthesizing replacement ketone compounds and a preparation method, and belongs to the field of chemical materials and medicines. A nitrogen-phosphorus-containing ligand is obtained through organic synthesis, the ligand is combined with iridium chloride and then loaded on a carrier of MCM-41 to prepare an iridium catalyst containing the MCM-41 loaded with thenitrogen-phosphorus-containing ligand. The catalyst prepared by the preparation method can be used to catalyzed synthesis of the replacement ketone compounds and synthesis of bisphenol F. The novel iridium heterogeneous catalyst containing the nitrogen-phosphorus-containing ligand is an environmentally friendly catalyst, compared with previous experimental schemes for synthesizing ketones, the catalyst has the advantages that the catalytic efficiency is high, the reaction conditions are mild, and the catalyst can be reused, and the catalyst is in line with the development concept of environmental protection and atomic economy; and when the catalyst is used in the synthesis reaction of bisphenol F, the catalytic activity is high, the application range is wide, and the application prospectsare good.

Description

technical field [0001] The invention relates to a catalyst and a preparation method for synthesizing substituted ketone compounds, which belong to the field of chemical materials and medicines. Background technique [0002] Due to their special structures, substituted ketones are important intermediates in organic synthesis. Because of its bright prospects in organic synthesis, it has received extensive attention and research interest from scientists at home and abroad in recent years. The traditional method of synthesizing functionalized carbonyl compounds is to complete the reaction under relatively harsh conditions, generally requiring conditions such as strong acid and strong base or using toxic halogenated hydrocarbons and other reagents. In recent years, with the increasing awareness of environmental protection To improve, seeking a green, efficient, environmentally friendly, preferably recyclable catalyst for the synthesis of substituted ketones has become the focus ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07C37/20C07C39/16C07C45/68C07C49/782C07C49/84C07C49/813C07F15/00
CPCB01J31/1616B01J31/189B01J2531/827C07C37/20C07C45/68C07F15/004C07C49/782C07C49/84C07C39/16C07C49/813
Inventor 王大伟李家豪桑欣欣倪才华胡文康
Owner JIANGNAN UNIV
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