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Oxidation synthesis method for ketonic beta-C-H bond acetyl

A technology for oxidative synthesis and bond acetylation, which is applied in the field of acetylation oxidation synthesis of β-position C-H bonds of ketones, can solve the problems of difficult synthesis of raw materials, difficulty in large-scale production, and high cost, and achieve environmental protection, small side reactions, and high reaction rate The effect of mild conditions

Inactive Publication Date: 2016-12-21
YUNNAN MINZU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the raw materials required by all synthetic methods are difficult to synthesize and expensive, making it difficult to produce on a large scale

Method used

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  • Oxidation synthesis method for ketonic beta-C-H bond acetyl

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A method for synthesizing acetylation of β-position C-H bonds of ketones, comprising the steps of:

[0023] (1) Sample response

[0024] Select a reaction flask with a capacity of 25mL, then add iodophenoxyketone acetate, iodobenzene diacetate, palladium acetate, glycine, KI, acetic acid and a mixed solvent of water in the reaction flask to react, and pass into the reaction flask while reacting Oxygen, the amount of said oxygen is 7atm, after the reaction a reaction mixture is formed, the temperature during said reaction is 80°C, the time of said reaction is 10h, the consumption of iodophenoxyketone acetate is 8mmol, the consumption of iodobenzene diacetate is 20mmol, the consumption of palladium acetate is 0.5mmol, the consumption of described glycine is 18mmol, the consumption of the mixed solvent of described acetic acid and water is 8mL, the consumption of described KI is 0.2equiv;

[0025] (2) cooling

[0026] The reaction mixture is cooled in a cooling box until...

Embodiment 2

[0032] A method for synthesizing acetylation of β-position C-H bonds of ketones, comprising the steps of:

[0033] (1) Sample response

[0034] Select a reaction flask with a capacity of 25mL, then add iodophenoxyketone acetate, iodobenzene diacetate, palladium acetate, glycine, KI, acetic acid and a mixed solvent of water in the reaction flask to react, and pass into the reaction flask while reacting Oxygen, the amount of said oxygen is 8atm, after the reaction a reaction mixture is formed, the temperature during said reaction is 100°C, the time of said reaction is 12h, the consumption of iodophenoxyketone acetate is 10mmol, the consumption of iodobenzene diacetate is 20mmol, the consumption of palladium acetate is 0.75mmol, the consumption of described glycine is 20mmol, the consumption of the mixed solvent of described acetic acid and water is 10mL, the consumption of described KI is 1.0equiv;

[0035] (2) cooling

[0036] The reaction mixture is cooled in a cooling box u...

Embodiment 3

[0042] A method for synthesizing acetylation of β-position C-H bonds of ketones, comprising the steps of:

[0043] (1) Sample response

[0044] Select a reaction flask with a capacity of 25mL, then add iodophenoxyketone acetate, iodobenzene diacetate, palladium acetate, glycine, KI, acetic acid and a mixed solvent of water in the reaction flask to react, and pass into the reaction flask while reacting Oxygen, the amount of oxygen is 9atm, and a reaction mixture is formed after the reaction, the temperature during the reaction is 120°C, the reaction time is 14h, the amount of iodophenoxyketone acetate is 12mmol, and the amount of iodobenzene diacetate is 20mmol, the consumption of palladium acetate is 1mmol, the consumption of described glycine is 22mmol, the consumption of the mixed solvent of described acetic acid and water is 12mL, the consumption of described KI is 2.2equiv;

[0045] (2) cooling

[0046] The reaction mixture is cooled in a cooling box until the temperatur...

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Abstract

The invention discloses an oxidation synthesis method for ketonic beta-C-H bond acetyl. The C-H bond of the original raw material is directly activated, so that the C-O bond construction is effectively realized in one step; the requirements for green chemistry and atom economy are met; the reaction condition is mild; the energy consumption is low; the process flow is simple; the side reaction is small; the yield is high and reaches 85% or above; the method is worthy of industrial popularization; the method is beneficial to environmental protection; obvious economic benefit and social benefit can be created; the market potential is huge; the prospect is wide.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry, and more specifically, the invention relates to a method for synthesizing acetylation of a β-position C-H bond of a ketone. Background technique [0002] β-acetyl ester ketone compounds are a kind of colorless to light yellow oily liquid, which are widely used in natural products, multifunctional materials and some drugs with physiological activity. It is mainly used as a food flavor enhancer, and can also be used to prepare various furan derivatives. It is an intermediate in the synthesis of medicines, pesticides, and fine chemicals, and is an important basic chemical raw material. At present, the methods for synthesizing β-acetyl ester ketone compounds at home and abroad mainly include: 1. Natural product extraction method; 2. Chemical method, that is, the reaction of β-hydroxyketone and acetyl chloride, or the reaction of aldol condensation reaction with acetyl chloride , again usin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/12C07C67/00C07C69/157
CPCC07B41/12C07C67/00C07C69/157
Inventor 谷利军李干鹏张洪涛李伟黄宝绪王长征
Owner YUNNAN MINZU UNIV