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One-step method for preparing alpha-halogenated acetophenone glycol ketal compound

A technology of halogenated acetophenone diol ketal and compound, which is applied in the field of organic compound preparation, can solve the problems of difficult post-processing, etc., and achieve the effects of simple post-processing, cost saving, and convenient operation

Inactive Publication Date: 2014-12-24
HUANGSHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, a one-step method for synthesizing α-haloacetophenone dimethyl acetals has been reported: using AlCl 3 Reacting with sodium persulfate to generate elemental chlorine in situ as a chlorine source, chlorinating acetophenone compounds and preparing α-chloroacetophenone dimethyl acetal compounds in one pot in the presence of methyl orthoformate (Zhou Zhong- shi, Li Li, He Xue-hua, J.Chem.Res.,2013,10,633), this method is very effective for acetophenone compounds containing strong electron-withdrawing substituents; Zhou Bin and Zou Xinzhuo reported the use of dihalogenated Because hydantoin is a halogenating agent, the corresponding α-halogenated acetophenone dimethyl ketal (CN101624321A) has been prepared by the reaction of acetophenone compounds and methanol in one-step method, and the yield can reach 80~94%, but the method uses amine Compounds are used as catalysts, and a large amount of molecular sieves are used as dehydrating agents, so post-treatment is difficult

Method used

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  • One-step method for preparing alpha-halogenated acetophenone glycol ketal compound
  • One-step method for preparing alpha-halogenated acetophenone glycol ketal compound
  • One-step method for preparing alpha-halogenated acetophenone glycol ketal compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Preparation of α-chloroacetophenone ethylene glycol ketal with chlorine as halogenated reagent

[0026] 10 mmol of acetophenone, 12 mmol of chlorine, 12 mmol of ethylene glycol, stirred for 1 h at 20°C, stopped the reaction, added 10 mL of ethyl acetate, extracted, recovered excess ethylene glycol, washed the ethyl acetate layer three times with 30 mL of water, anhydrous sodium sulfate dry. Filtration, rotary evaporation to obtain α-chloroacetophenone glycol ketal, the yield is 82%. 1 H NMR (CDCl 3 ,300MHz)δ3.75(2H,s),3.90-3.92(2H,m),4.15-4.19(2H,m),7.25-7.39(3H,m),7.51-7.53(2H,m).

Embodiment 2

[0027] Example 2 Preparation of α-chloroacetophenone glycol ketal with dichlorohydantoin halogenation reagent

[0028] 10 mmol of acetophenone, 5 mmol of dichlorohydantoin, 12 mmol of ethylene glycol, 30°C, stirring for 6 h to stop the reaction, add 10 mL of ethyl acetate, extract, recover excess ethylene glycol, wash the ethyl acetate layer with 30 mL of water three times, no Dry over sodium sulfate. Filtration, rotary evaporation to obtain α-chloroacetophenone glycol ketal, the yield is 84%.

Embodiment 3

[0029] Example 3 Preparation of α-chloroacetophenone glycol ketal with dichlorohydantoin halogenation reagent

[0030] 10 mmol of acetophenone, 8 mmol of dichlorohydantoin, 20 mmol of ethylene glycol, at 30°C, stirred for 6 h, the reaction was stopped, 10 mL of ethyl acetate was added, extracted, and the excess ethylene glycol was recovered. The ethyl acetate layer was washed three times with 30 mL of water. Dry over sodium sulfate. Filtration, rotary evaporation to obtain α-chloroacetophenone glycol ketal, the yield is 95%.

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Abstract

The invention discloses a one-step method for preparing an alpha-halogenated acetophenone glycol ketal compound by acetophenone. The method is characterized in that acetophenone, halogenated reagents and glycol are simultaneously subjected to alpha-halogenating reaction and condensation reaction with the glycol by one step to obtain the alpha-halogenated acetophenone glycol ketal compound. According to the one-step method for preparing the alpha-halogenated acetophenone glycol ketal compound, two steps of original reactions are simplified to one step, other catalysts and dehydrating agents are not required, reaction conditions are gentle, the yield is high, costs are saved, the operation is convenient, and the post-processing is simple.

Description

Technical field [0001] The invention belongs to the technical field of organic compound preparation, and specifically relates to a one-step method for preparing α-haloacetophenone glycol ketal compounds. Background technique [0002] The α-halogenated (chlorine or bromine) products of various acetophenones are important organic synthesis intermediates and are widely used in the organic synthesis of fine chemicals such as pharmaceuticals, pesticides, dyes, and spices. However, since this type of molecule contains a carbonyl group and two active sites at the α-position, the carbonyl group is often protected in further reactions. In practical applications, the most common method is to react carbonyl compounds with cheap and easily available diols to form ketals. For example: in the synthesis of high-efficiency fungicides pentoconazole, fenoconazole, propiconazole and difenoconazole, α-haloacetophenone glycol ketals are key intermediates (Sun Jialong, Modern Pesticides Synthes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/16C07D317/22
CPCC07D317/16C07D317/22
Inventor 郑祖彪何在明吴新虎牛青龙吴成凤韩冰冰
Owner HUANGSHAN UNIV
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