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Novel method for synthesizing functionalized ketone through reaction of aromatic ketone and primary alcohol

An aromatic ketone, functionalization technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as harsh reaction conditions and toxicity

Inactive Publication Date: 2014-07-16
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, although there are many effective methods to achieve this conversion reaction, they usually require the use of harsh reaction conditions or toxic oxidants, resulting in a large amount of environmental pollutants

Method used

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  • Novel method for synthesizing functionalized ketone through reaction of aromatic ketone and primary alcohol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment one: a kind of new method of synthesizing functionalized ketone by aromatic ketone and primary alcohol reaction, comprises the following process steps:

[0022] Under nitrogen protection, in 50mL Schlenk tube, add acetophenone (120mg, 1mmol), benzyl alcohol (130mg, 1.2mmol), [(Bt) 2 *Ir*P(Ph) 3 ]Cl (10mg, 0.01mmol, 1.0mol%), cesium carbonate (326mg, 1.0mmol), and 2.0mL tert-amyl alcohol were added; the reaction solution was reacted at 120°C for 20h, and the resulting solution was separated with a 200-300 mesh silica gel column (washing Deliquification is 1: 10 ethyl acetate / petroleum ether), after removing the solvent, the corresponding product is obtained, and the structural formula is: White crystals, melting point: 72-74°C, yield: 92%.

Embodiment 2

[0023] Embodiment two: a kind of novel method of synthesizing functionalized ketone by aromatic ketone and primary alcohol reaction, comprises the following processing steps: under nitrogen protection, in 50mL Schlenk tube, add acetophenone (120mg, 1mmol), 3-hydroxymethyl Pyridine (131 mg, 1.2 mmol), [(Bt) 2 *Ir*P(Ph) 3 ]Cl (10mg, 0.01mmol, 1.0mol%), cesium carbonate (326mg, 1.0mmol), and 2.0mL tert-amyl alcohol were added; the reaction solution was reacted at 120°C for 20h, and the resulting solution was separated with a 200-300 mesh silica gel column (washing Deliquification is 1: 10 ethyl acetate / petroleum ether), after removing the solvent, the corresponding product is obtained, and the structural formula is: White crystals, melting point: 84-86°C, yield: 86%.

Embodiment 3

[0024] Embodiment three: a kind of new method of synthesizing functionalized ketone by aromatic ketone and primary alcohol reaction, comprises the following processing steps: under nitrogen protection, in 50mL Schlenk tube, add acetophenone (120mg, 1mmol), 4-hydroxymethyl Pyridine (131 mg, 1.2 mmol), [(Bt) 2 *Ir*P(Ph) 3 ]Cl (10mg, 0.01mmol, 1.0mol%), cesium carbonate (326mg, 1.0mmol), and 2.0mL tert-amyl alcohol were added; the reaction solution was reacted at 120°C for 20h, and the resulting solution was separated with a 200-300 mesh silica gel column (washing Deliquification is 1: 10 ethyl acetate / petroleum ether), after removing the solvent, the corresponding product is obtained, and the structural formula is: White crystals, melting point: 64-67°C, yield: 83%.

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Abstract

The invention discloses a novel method for synthesizing functionalized ketone through reaction of aromatic ketone and primary alcohol. According to the technical scheme, the method includes the following processing steps that (1) the aromatic ketone and aromatic methanol or fatty alcohol are added into a reaction container according to the molar ratio of 2:1-2, [(Bt)2*Ir*P(Ph)3]C1 is added as a catalyst (Bt is phenylbenzothiazole), alkali and an organic solvent are added, and reaction is conducted for 15-24 hours under the condition that the temperature is 100-150 DEG C, wherein the amount ratio of the aromatic ketone, the aromatic methanol or the fatty alcohol, the catalyst and the alkali is 2:1-2:0.01-0.02:1-2; (2) after reaction liquid obtained in the step (1) is filtered, the reaction liquid is purified by 200-300-mesh silicagel columns; after 20-50mL of petroleum ether is used for pre-leaching the silicagel columns, leacheate is used for conducting elution, wherein the flow velocity of the leacheate is 1-2 mL / min, and the elution time is 3-6 h; after the solvent is removed, a corresponding functionalized ketone is obtained. According to studies, it is discovered that the novel method is used for catalyzing the aromatic ketone and the aromatic methanol or the fatty alcohol to synthesize the functionalized ketone, and the method has the advantages that conditions are gentle, the conversion rate is high, and no pollutant is generated.

Description

technical field [0001] The invention relates to a new method for synthesizing functionalized ketones through the reaction of aromatic ketones and primary alcohols, belonging to the field of chemical materials and organic synthesis. Background technique [0002] With the increasingly prominent environmental problems, more attention has been paid to green chemistry, and the development of environmentally friendly catalytic systems and synthetic methods has attracted more and more attention of organic chemists. [0003] The selective oxidation of alcohols to the corresponding aldehydes and ketones is one of the most versatile functional group transformation reactions in organic synthesis, and has very important applications in both fundamental research and industrial organic synthesis. At present, although there are many effective methods for realizing the conversion reaction, harsh reaction conditions or toxic oxidants are usually required, resulting in a large amount of envir...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/04C07C49/782C07C49/76C07C45/68C07D213/50C07C205/45C07C201/12C07D307/46
Inventor 赵科研王大伟丁玉强苗红艳杨淑艳
Owner JIANGNAN UNIV
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