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A kind of preparation method of chloroalkoxy-1,3-diphenyl-β-diketone

A technology of chloroalkoxy and methoxyphenyl, which is applied in the field of organic compound synthesis, can solve the problems of low solvent selectivity, difficulty in purification, catalyst residue, etc. mild effect

Active Publication Date: 2022-08-05
FOSHAN HUAYOO PHOTOELECTRIC MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using high temperature reaction conditions, not only the solvent selectivity is small and the price is high, but the most important thing is that many organic molecules, especially drug molecules or functional material molecules are unstable and easy to decompose under high temperature conditions; choose to use precious metal catalysts such as palladium and rhodium to complete Catalytic reaction, there are catalyst residues in the process of producing drug molecules, it is not easy to purify, and the preparation cost is high

Method used

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  • A kind of preparation method of chloroalkoxy-1,3-diphenyl-β-diketone
  • A kind of preparation method of chloroalkoxy-1,3-diphenyl-β-diketone
  • A kind of preparation method of chloroalkoxy-1,3-diphenyl-β-diketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] To prepare 1-(3-chloro-4-methoxyphenyl)-3-phenyl-1,3-propanedione, its structural formula is as follows:

[0032]

[0033] Into a 100mL round-bottomed flask were added dry N,N-dimethylformamide 40mL, methyl 3,4-dichlorobenzoate 4.10g (20mmol), sodium hydride (60% content of solid paraffin mixture) 1.60g (40 mmol) and stirred at room temperature for 10 minutes. 2.88 g (24 mmol) of acetophenone was added in 4 batches at room temperature, and after stirring was continued for 30 minutes, the temperature was raised to 40° C. and stirring was continued for 3 hours. After cooling to room temperature, it was poured into 200 mL of ice water with stirring, acidified (neutralized with 36% hydrochloric acid) to weakly acidic, and then allowed to stand overnight. The above aqueous solution was poured out, and the organic viscous solid was recrystallized twice with a mixture of petroleum ether and ethyl acetate to obtain the target product with a yield of 75%. Its H NMR and C NM...

Embodiment 2

[0036] To prepare 1-(3-chloro-4-methoxyphenyl)-3-(4-methoxyphenyl)-1,3-propanedione, its structural formula is as follows:

[0037]

[0038] The difference between this example and Example 1 is that the target product was prepared by using 4-methoxyacetophenone instead of acetophenone, and the yield was 71%. Its H NMR and C NMR results are as follows: 1 H NMR (300MHz, CDCl 3 )δ:7.99-7.93(m,3H),7.86(dd,J 1 =8.4Hz,J 2 = 2.4Hz, 1H), 6.99-6.95(m, 3H), 6.67(s, 1H), 3.96(s, 3H), 3.87(s, 3H). 13 C NMR (75MHz, CDCl 3 )δ: 184.8, 183.3, 163.2, 158.1, 129.2, 129.0, 127.8, 127.3, 122.9, 114.0, 111.5, 91.6, 56.3, 55.5.DEPT135(75MHz, CDCl 3 )δ: 129.2(CH), 127.3(CH), 114.0(CH), 111.5(CH), 91.6(CH), 56.3CH 3 ),55.5CH 3 ).

Embodiment 3

[0040] To prepare 1-phenyl-3-(4-chloro-2-methoxyphenyl)-1,3-propanedione, its structural formula is as follows:

[0041]

[0042] Method 1: The difference between the method 1 of this embodiment and the embodiment 1 is that the target product is prepared by using methyl 2,4-dichlorobenzoate instead of methyl 3,4-dichlorobenzoate, and the yield is 65%. Its H NMR and C NMR results are as follows: 1 H NMR (300MHz, CDCl 3 )δ: 7.96-7.88(m, 3H), 7.54-7.47(m, 3H), 7.06(s, 1H), 7.03-6.98(m, 2H), 3.95(s, 3H). 13 C NMR (75MHz, CDCl 3 )δ: 186.1, 182.8, 159.0, 138.9, 135.8, 132.3, 131.4, 128.6, 127.2, 123.4, 121.1, 112.3, 98.4, 56.1.DEPT135 (75MHz, CDCl 3 )δ: 132.4(CH), 131.4(CH), 128.6(CH), 127.2(CH), 121.2(CH), 112.4(CH), 98.4(CH), 56.1(CH) 3 ).

[0043] Method 2: The difference between Method 2 in this example and Example 1 is that the target product is prepared by using methyl 2-fluoro-4-chlorobenzoate instead of methyl 3,4-dichlorobenzoate. Its H NMR and C NMR results are as...

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Abstract

The invention belongs to the technical field of organic synthesis and discloses a preparation method of chloroalkoxy-1,3-diphenyl-β-diketone. The preparation method includes the following steps: dissolving the compound represented by the formula (I) and the base in a solvent, adding the compound represented by the formula (II), and reacting to prepare the chloroalkoxy-1,3-di Phenyl-β-diketone; in formula (I), R1 is selected from C1-4 alkyl; X1, X2, X3, X4, X5 independently represent a halogen atom or a hydrogen atom; in formula (II), R2 One selected from hydrogen, C1-18 alkyl, alkoxy, aryl or aryloxy, the preparation method has mild reaction conditions, does not require high temperature conditions and uses precious metal catalysts; and the reaction raw materials are readily available, and the reaction needs wide solvent selectivity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of chloroalkoxy-1,3-diphenyl-β-diketone. Background technique [0002] β-diketones are widely used in the preparation of catalysts, stabilizers, chelating agents, ultraviolet absorbers, pharmaceutical preparations and optoelectronic materials. For example, 1-(3-chloro-4-methoxyphenyl)-3-(4-methoxyphenyl)-1,3-propanedione can be used as nonlinear optical material; 1-(tert-butylbenzene) β-diketones are also intermediates of boron-based luminescent materials. [0003] 1,3-Diphenyl-β-diketones are important β-diketones. 1,3-Diphenyl-β-diketones are usually prepared by the condensation of benzoic acid esters with acetophenone under the action of sodium alkoxide. If it is desired to introduce an alkoxy group into the benzene ring of the 1,3-diphenyl-β-diketone compound, the general method is to select the corresponding alkoxybenzoate or alkoxyacetophen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/84C07C45/45
CPCC07C45/455C07C49/84
Inventor 宋森川刘洋史华红梁东
Owner FOSHAN HUAYOO PHOTOELECTRIC MATERIAL CO LTD