Ketone compound and synthesis method thereof

A technology of ketone compounds and synthetic methods, which is applied in the field of organic synthesis, can solve the problems of poor substrate applicability, high toxicity of oxidants, unfavorable industrial production, etc., and achieve the effects of easy preparation and storage, less by-products, and high-efficiency methods

Active Publication Date: 2017-10-13
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Based on the above relevant domestic and foreign literature and patent reports, the methods used all require high-valent compounds as oxidants, the oxidants used are highly toxic, and the reaction temperature is very high, and the substrate applicability is not wide, which is not conducive to industrial production.

Method used

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  • Ketone compound and synthesis method thereof
  • Ketone compound and synthesis method thereof
  • Ketone compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1 synthesizes benzophenone

[0031] Weigh 0.1mmol tetraphenylethylene glycol, 0.2mmol 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane di(tetrafluoroborate) salt (SelectFlour) into 15mL A magnetic stirrer and 2mL N,N-dimethylformamide (DMF) were added to a pressure-resistant reaction tube, and the reaction was stirred at 80°C for 20h, as shown in formula (1). After the reaction, wash off the solvent with 10 mL of water, extract with 10 mL of ethyl acetate, dry with anhydrous sodium sulfate at 25°C for 15 minutes and filter, and finally use a rotary evaporator at -0.09MPa, 40°C to carry out vacuum distillation to remove organic solvent, the product benzophenone can be obtained, and the yield is 90%.

[0032] figure 1 is the NMR characterization collection of benzophenone, wherein, figure 1 for benzophenone 1 HNMR spectrum, figure 2 for benzophenone 13 C NMR spectrum. Benzophenone was confirmed by NMR characterization and the characteristic structu...

Embodiment 2

[0034] Example 2 Synthesis of 4,4'-dimethylbenzophenone

[0035] Weigh 0.1mmol 1,1,2,2-tetra-p-tolylethane-1,2-diol, 0.2mmol 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2 ] Octane bis(tetrafluoroborate) salt was added to a 15mL pressure-resistant reaction tube, a magnetic stirrer and 2mL N,N-dimethylformamide were added, and the reaction was stirred at 80°C for 20h, as shown in formula (2). After the reaction, wash off the solvent with 10 mL of water, extract with 10 mL of ethyl acetate, dry with anhydrous sodium sulfate at 25°C for 15 minutes and filter, and finally use a rotary evaporator at -0.09MPa, 40°C to carry out vacuum distillation to remove organic solvent, the product 4,4'-dimethylbenzophenone can be obtained with a yield of 85%.

[0036] The NMR characterization spectrum of 4,4'-dimethylbenzophenone is as follows image 3 and Figure 4 shown. in, image 3 4,4'-Dimethylbenzophenone 1 HNMR spectrum, Figure 4 4,4'-Dimethylbenzophenone 13 C NMR spectrum. 4,4...

Embodiment 3

[0038] Example 3 Synthesis of 4,4'-dichlorobenzophenone

[0039]Weigh 0.1mmol 1,1,2,2-tetra-p-chlorophenylethane-1,2-diol, 0.2mmol 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2. 2] Add octane bis(tetrafluoroborate) salt into a 15mL pressure-resistant reaction tube, add a magnetic stirrer and 2mL N,N-dimethylformamide, stir and react at 80°C for 20h, as shown in formula (3). After the reaction, the solvent was washed with 10 mL of water, extracted with 10 mL of ethyl acetate, dried with anhydrous sodium sulfate at 25°C for 10 minutes and filtered, and finally removed by vacuum distillation with a rotary evaporator at -0.095MPa and 35°C. organic solvent, the product 4,4'-dichlorobenzophenone can be obtained with a yield of 88%.

[0040] The NMR characterization spectrum of 4,4'-dichlorobenzophenone is as follows Figure 5 and Figure 6 shown. in, Figure 5 of 4,4'-dichlorobenzophenone 1 H NMR spectrum, Figure 6 of 4,4'-dichlorobenzophenone 13 C NMR spectrum. 4,4'-dichlo...

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Abstract

The invention discloses a method for generation of a ketone compound from a vicinal diol compound. The method includes: dissolving the vicinal diol compound in a solvent, and then under the action of the oxidizing agent 1-chloromethyl-4-fluoro-1, 4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate), enabling carbon-carbon bond breakage of the vicinal diol compound to generate the ketone compound. The method provided by the invention has the advantages of no need for adding of a metal chelating agent, low reaction temperature, no by-product formation, high conversion rate, and a product yield of 56%-90%, thus being an environment-friendly method.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and more specifically relates to a method for ketone compounds. Background technique [0002] The oxidative cleavage of carbon-carbon bonds of vicinal diols to form ketones is an important reaction in organic synthesis (Adv.Carbohydr.Chem.Biochem.2006,60,183-250). For example with BiPh 3 / NBS / K 2 CO 3 ,CrO 3 ,NIS,Ta(NO 3 ) 3 , CAN etc. are used as oxidizing agents to oxidize and break the carbon-carbon bonds of adjacent diol compounds at a reaction temperature of 120°C (J.Chem.Soc., Chem.Commun., 1981, 1232–1233; Can.J.Chem., 1966, 44, 1323–1324; J.Org.Chem., 1981, 46, 1927–1929; J.Org.Chem., 1972, 37, 4204–4206; J.Org.Chem., 1969, 34, 869–871 .). Based on the above relevant domestic and foreign literature and patent reports, the methods used all require high-valent compounds as oxidants, the oxidants used are highly toxic, and the reaction temperature is high, and the substrate...

Claims

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Application Information

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IPC IPC(8): C07C45/29C07C45/82C07C49/786C07C49/784C07C201/12C07C201/16C07C205/45
CPCC07C45/29C07C45/82C07C49/784C07C49/786C07C201/12C07C201/16C07C205/45
Inventor 陈迁黄昱霖温春晓晏鑫星曾洁坤王肖峰霍延平杜志云张焜
Owner GUANGDONG UNIV OF TECH
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