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Method for synthesizing methyl ketone

A technology of methyl ketone and synthesis reaction, which is applied in hydrolysis to prepare carbonyl compounds, carbon-carbon triple bond hydration preparation, organic chemistry, etc. It can solve long-term problems, achieve broad development prospects, and shorten the reaction time.

Inactive Publication Date: 2015-04-29
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

In recent years, gold complexes have gradually replaced toxic mercury salts to catalyze this reaction (a) E.Mizushima, K.Sato, T.Hayashi, M.Tanaka, Angew.Chem.Int.Ed.2002,41, 4563-4565; b) R. Casado, M. Contel, M. Laguna, P. Romero, S. Sanz, J. Am. Chem. Soc. 2003, 125, 11925-11935; c) N. Marion, R. S. Ramon , S.P.Nolan, J.Am.Chem.Soc.2009,131,448-449). However, the reaction also takes a long time

Method used

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  • Method for synthesizing methyl ketone
  • Method for synthesizing methyl ketone
  • Method for synthesizing methyl ketone

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1: acetophenone

[0021] Acetophenone

[0022]

[0023] Catalyst A (6mg, 0.01mmol, 1.0mol%), AgOTf (2.6mg, 0.01mmol, 1.0mol%), phenylacetylene (102mg, 1mmol), 1,4-dioxane (1ml) and water (36ul ) were sequentially added to 5ml microwave tubes. The reaction mixture was microwaved at 120 °C for 1 hour and then cooled to room temperature. Filtrate, remove the solvent by rotary evaporation, and then obtain the pure target compound by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 92%

[0024] 1 H NMR (500MHz, CDCl 3 )δ7.96(dd,J=7.6Hz and0.7Hz,2H,ArH),7.57(t,J=7.5Hz,1H,ArH),7.47(t,J=7.7Hz,2H,ArH),2.61( s,3H,CH 3 ).

Embodiment 2

[0025] Embodiment 2:4-methylacetophenone

[0026] 1-p-tolylethanone

[0027]

[0028] Catalyst A (6mg, 0.01mmol, 1.0mol%), AgOTf (2.6mg, 0.01mmol, 1.0mol%), 4-methylphenylacetylene (116mg, 1mmol), 1,4-dioxane (1ml) and water (36ul) were sequentially added to a 5ml microwave tube. The reaction mixture was microwaved at 120 °C for 1 hour and then cooled to room temperature. Filtrate, remove the solvent by rotary evaporation, and then obtain the pure target compound by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 93%

[0029] 1 H NMR (500MHz, CDCl 3 )δ7.86(d,J=7.9Hz,2H,ArH),7.27(d,J=6.4Hz,2H,ArH),2.59(s,3H,CH 3 ),2.42(s,3H,CH 3 ).

Embodiment 3

[0030] Embodiment 3:4-methoxyacetophenone

[0031] 1-(4-methoxyphenyl)ethanone

[0032]

[0033] Catalyst A (6mg, 0.01mmol, 1.0mol%), AgOTf (2.6mg, 0.01mmol, 1.0mol%), 4-methoxyphenylacetylene (132mg, 1mmol), 1,4-dioxane (1ml ) and water (36ul) were sequentially added to a 5ml microwave tube. The reaction mixture was microwaved at 120 °C for 1 hour and then cooled to room temperature. Filtration, rotary evaporation to remove the solvent, and then column chromatography (developing solvent: petroleum ether / ethyl acetate) to obtain the pure target compound, yield: 94%

[0034] 1 H NMR (500MHz, CDCl 3 )δ7.94(d,J=8.8Hz,2H,ArH),6.94(d,J=8.8Hz,2H,ArH),3.88(s,3H,OCH 3 ),2.57(s,3H,CH 3 ).

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Abstract

The invention discloses a method for synthesizing methyl ketone. The method comprises the following steps: adding alkyne, [(IPr)AuCl], AgOTf, a solvent, namely 1,4-dioxane and water in a reaction container, performing microwave reaction on a reaction mixture for 1h at 120 DEG C and cooling to room temperature; filtering, performing rotary evaporation to remove the solvent, and then separating by a column to obtain a target compound. The method disclosed by the invention adopts a microwave technology, and the reaction time is shortened; furthermore, the reaction only generates a byproduct, namely water, so that the reaction is in line with the requirements of green chemistry and has broad development prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a method for synthesizing ketones. Background technique [0002] Methyl ketones are a very important class of compounds, exhibiting a wide range of physiological and pharmacological activities, and are also important intermediates in organic synthesis. Transition metal-catalyzed regioselective hydrolysis of alkynes is an important method for the synthesis of methyl ketones. In recent years, gold complexes have gradually replaced toxic mercury salts to catalyze this reaction (a) E.Mizushima, K.Sato, T.Hayashi, M.Tanaka, Angew.Chem.Int.Ed.2002,41, 4563-4565; b) R. Casado, M. Contel, M. Laguna, P. Romero, S. Sanz, J. Am. Chem. Soc. 2003, 125, 11925-11935; c) N. Marion, R. S. Ramon , S.P.Nolan, J.Am.Chem.Soc.2009, 131, 448-449). However, the reaction still needs a long time. [0003] Microwave technology has been more and more developed and widely u...

Claims

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Application Information

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IPC IPC(8): C07C49/78C07C49/807C07C49/84C07C49/533C07C45/42
CPCC07C45/26C07C49/78C07C49/76C07C49/807C07C49/84C07C49/533
Inventor 马娟渠攀攀李峰
Owner NANJING UNIV OF SCI & TECH
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