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Preparation method of chloroalkoxy-1, 3-diphenyl-beta-diketone

A chloroalkoxy, methoxyphenyl technology, applied in the field of organic synthesis, can solve the problems of catalyst residue, unstable and easy to decompose, difficult to purify, etc.

Active Publication Date: 2021-09-14
佛山华铕光电材料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Preparation method of chloroalkoxy-1, 3-diphenyl-beta-diketone
  • Preparation method of chloroalkoxy-1, 3-diphenyl-beta-diketone
  • Preparation method of chloroalkoxy-1, 3-diphenyl-beta-diketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0032]

[0033] Add 40 mL of dry N,N-dimethylformamide, 4.10 g (20 mmol) of methyl 3,4-dichlorobenzoate, and 1.60 g of sodium hydride (60% solid paraffin mixture) into a 100 mL round bottom flask. (40mmol), stirred at room temperature for 10 minutes. At room temperature, 2.88 g (24 mmol) of acetophenone was added in 4 batches. After stirring 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 weak acidity, and left to stand overnight. The above aqueous solution was poured off, and the viscous organic solid was recrystallized twice from a mixture of petroleum ether and ethyl acetate to obtain the target product with a yield of 75%. Its proton nuclear magnetic resonance spectru...

Embodiment 2

[0036] Preparation of 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 with 4-methoxyacetophenone instead of acetophenone, and the yield was 71%. Its proton nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum result 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] Preparation of 1-phenyl-3-(4-chloro-2-methoxyphenyl)-1,3-propanedione, its structural formula is as follows:

[0041]

[0042] Method 1: The difference between Method 1 of this example and Example 1 is that methyl 2,4-dichlorobenzoate is used instead of methyl 3,4-dichlorobenzoate to prepare the target product with a yield of 65%. Its proton nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum result are as follows: 1 HNMR (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 of this example and Example 1 is that methyl 2-fluoro-4-chlorobenzoate is used instead of methyl 3,4-dichlorobenzoate to prepare the targe...

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Abstract

The invention belongs to the technical field of synthesis of organic matters, and discloses a preparation method of chloroalkoxy-1, 3-diphenyl-beta-diketone. The preparation method comprises the steps of dissolving a compound as shown in a formula (I) defined in the description and alkali in a solvent, adding a compound as shown in a formula (II) defined in the description, and reacting to prepare the chloroalkoxy-1, 3-diphenyl-beta-diketone, wherein in the formula (I), R1 is selected from C1-4 alkyl; X1, X2, X3, X4 and X5 each independently represent a halogen atom or a hydrogen atom; in the formula (II), R2 is selected from one of hydrogen, C1-18 alkyl, alkoxy, aryl or aryloxy, the reaction condition of the preparation method is mild, and a high-temperature condition and use of a noble metal catalyst are not needed; and the reaction raw materials are easily available, and the selectivity of the solvent required by the reaction is wide.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a preparation method of chloroalkoxy-1,3-diphenyl-β-diketone. Background technique [0002] β-diketone compounds are widely used in the preparation of catalysts, stabilizers, chelating agents, ultraviolet absorbers, pharmaceutical preparations and photoelectric materials. For example, 1-(3-chloro-4-methoxyphenyl)-3-(4-methoxyphenyl)-1,3-propanedione can be used as nonlinear optical material; 1-(tert-butylbenzene Base)-3-(4-methoxyphenyl)-1,3-propanedione is an active ingredient in sunscreen products with UV-absorbing effect; β-diketone compounds 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 condensed with acetophenone by benzoate ester under the action of sodium alkoxide. If it is desired to introduce an alkoxy group on the benzene rin...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/45
CPCC07C45/455C07C49/84
Inventor 宋森川刘洋史华红梁东
Owner 佛山华铕光电材料股份有限公司
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