Synthetic method for diaryl ketone compounds

A technology for diaryl ketones and synthesis methods, which is applied in the field of synthesis of diaryl ketones, can solve problems such as complicated operations, equipment corrosion, and difficult separations, and achieve high product selectivity, mild reaction conditions, and simplified The effect of the action steps

Active Publication Date: 2015-11-11
邳州市润宏实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The acylation method mostly uses aluminum trichloride as a catalyst, and reacts with substituted benzene and substituted benzoyl chloride as raw materials. Because there are many isomers in the target product, it is difficult to separate, and a large amount of waste acid is generated during the reaction process, which corrodes production Equipment; the carbonylation method generally reacts under high temperature and high pressure, and the operation is complicated, and one of the raw materials used is carbon monoxide, which is more dangerous; the nitric acid oxidation method uses nitric acid to oxidize diphenylmethane compounds, and the reaction time of this method is long. Equipment Severe corrosion, difficult product post-processing

Method used

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  • Synthetic method for diaryl ketone compounds
  • Synthetic method for diaryl ketone compounds
  • Synthetic method for diaryl ketone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the preparation of benzophenone (formula (2-1))

[0030] Add diphenylmethanol acetate (formula (1-1), 0.45g, 2mmol), DDQ (0.45g, 2mmol), H 2 O (0.18g, 10mmol) and chlorobenzene (8ml) were reacted with stirring at 130°C, monitored by TLC, and reacted for 2h. The reaction solution was sampled and analyzed by gas chromatography (GC). The conversion rate was 100%, and the product selectivity was 99%. The reaction liquid was evaporated to remove the solvent under reduced pressure, passed through a silica gel column, and a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:200 was used as the eluent to collect the eluate containing the target compound, evaporated to remove the solvent, and then dried to obtain two Benzophenone 0.35g, the isolated yield of benzophenone is 97%.

Embodiment 2

[0031] Embodiment 2: the preparation of benzophenone (formula (2-1))

[0032] The reaction steps were the same as in Example 1, except that chlorobenzene was changed to o-dichlorobenzene, and the reaction was stirred at 140° C. for 1.5 hours. The reaction conversion rate was 100%, and the product selectivity was 99%. Finally, 0.35 g of benzophenone was obtained, and the isolated yield of benzophenone was 97%.

Embodiment 3

[0033] Embodiment 3: the preparation of phenyl o-tolyl ketone (formula (2-2))

[0034] Add phenyl-o-tolylmethanol acetate (formula (1-2), 0.48g, 2mmol), DDQ (0.54g, 2.4mmol), H 2 O (0.18g, 10mmol) and chlorobenzene (8ml) were reacted under stirring at 130°C, monitored by TLC, and reacted for 3h. The reaction solution was sampled and analyzed by gas chromatography (GC). The conversion rate was 98%, and the product selectivity was 99%. The reaction solution was evaporated to remove the solvent under reduced pressure, passed through a silica gel column, and the mixture of ethyl acetate and petroleum ether with a volume ratio of 1:200 was used as the eluent to collect the eluate containing the target compound, evaporated to remove the solvent, and then dried to obtain benzene 0.37 g of phenyl-o-tolyl ketone, and the isolated yield of phenyl-o-tolyl ketone was 95%.

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Abstract

The invention provides a synthetic method for diaryl ketone compounds. The method comprises the following steps: adding ester derivatives of raw material diaryl methanol, DDQ and water into an organic solvent, carrying out stirring, then carrying out heating to 110 to 140 DEG C and carrying out reaction for 0.5 to 12 h, and subjecting obtained reaction liquid to after-treatment so as to obtain the diaryl ketone compounds, wherein the ester derivatives of the raw material diaryl methanol have a structural formula as shown in a formula (V), (VI), (VII) or (VIII), and one-to-one correspondingly obtained products have the structural formula as shown in the formula (I), (II), (III) or (IV). The synthetic method for the diaryl ketone compounds provided by the invention has the advantages of simple, convenient and safe operation, mild reaction conditions and high product selectivity.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing diaryl ketone compounds. (2) Background technology [0002] Diaryl ketones have special physical, chemical and biological properties. These compounds can be used as intermediates for drug synthesis, monomers for the synthesis of high-performance engineering plastics, and ultraviolet absorbers. They have been widely used in plastics, cosmetics, Coatings, agrochemicals and electronics industries and other fields. Among the diaryl ketone compounds, benzophenone is the simplest in structure. This compound is a transparent crystal at normal temperature and pressure. It is an important intermediate in organic synthesis and an important additive in fine chemicals. It is widely used in organic coatings and medicines. Synthesis, plastics, flavors and fragrances, UV absorbers for polymer materials, photosensitizers for film coatings, etc. In addition, diaryl ketone compounds are the most widely studied pho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/00C07C49/784C07C49/786C07C49/788C07C49/813C07C49/84C07D213/50C07D333/22C07B41/06
CPCC07B41/06C07C45/00C07C49/784C07C49/786C07C49/788C07C49/813C07C49/84C07D213/50C07D333/22
Inventor 沈振陆马佳颀胡志明李美超胡信全莫卫民
Owner 邳州市润宏实业有限公司
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