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Synthesis method of benzodioxyheterohexenone aromatic compounds

A benzodioxanone aromatic and synthetic method technology, applied in the direction of organic chemistry and the like, can solve the problems of harsh reaction conditions, unfriendly strong acid, narrow substrate range, etc., and achieves short reaction time, green post-processing, Wide range of substrate effects

Active Publication Date: 2014-04-09
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The technical problem to be solved by the present invention is to provide a synthetic method of benzodioxenone aromatic compound, which solves the problems of narrow substrate range, harsh reaction conditions, long reaction time, many by-products and high yield in existing synthetic methods. Low efficiency, need strong acid and other environmental problems

Method used

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preparation example Construction

[0015] The invention relates to a method for synthesizing a benzodioxanone aromatic compound. The method is as follows: adding halogenated alkane, salicylic acid or substituted salicylic acid, and a base into an organic solvent, and the temperature is 60-130° C. The reaction is carried out for 5 to 10 hours, and the final separation and purification can be performed; the halogenated alkane is dichloro, dibromo or diiodo alkane; the amount ratio of the salicylic acid or substituted salicylic acid to the base is 1: 1 to 3 .

[0016] The separation and purification are as follows: after the reaction is completed, it is lowered to room temperature, water is added, extracted with ethyl acetate, dried, concentrated, and purified to obtain the product.

[0017] The substituent of the substituted salicylic acid is one of an alkyl group, an alkoxy group, an amino group and a halogen.

[0018] The base is one of potassium bicarbonate, potassium carbonate, cesium carbonate, dipotassium ...

Embodiment 1

[0027] Preparation of 4H-benzo[d][1,3]dioxen-4-one

[0028] 0.5mmol of salicylic acid, K 3 PO 4 ·7H 2 O1mmol, 0.6mL of dichloromethane, 1.5mL of N,N'-dimethylformamide were added to a 10mL reaction tube, placed in an oil bath at 100°C, and reacted for 6h. The reaction was stopped and cooled to room temperature. The reaction solution was diluted with ethyl acetate, washed with water three times, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter and concentrate to obtain 74.25 mg of the target product with a yield of 99%.

[0029] The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 ):δ7.99(d,J=7.8Hz,1H),7.58(dd,J=12.2,4.8Hz,1H),7.19(t,J=7.6Hz,1H),7.07(d,J=8.3Hz ,1H),5.66(s,2H); 13 C NMR (100MHz, CDCl 3 ):δ161.29,158.39,136.22,130.30,123.51,116.63,116.61,116.59,114.85,91.05.

Embodiment 2

[0031] Preparation of 8-methyl-4H-benzo[d][1,3]dioxen-4-one 0.5 mmol of 3-methylsalicylic acid, K 3 PO 4 ·3H 2 O1mmol, 0.6mL of dichloromethane, 1.5mL of N,N'-dimethylformamide were added to a 10mL reaction tube, placed in an oil bath at 100°C, and reacted for 6h. The reaction was stopped and cooled to room temperature. The reaction solution was diluted with ethyl acetate, washed with water three times, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter and concentrate to obtain 81.18 mg of the target product with a yield of 99%.

[0032] The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 ): δ7.81(d,J=7.8Hz,1H),7.49–7.35(m,1H),7.06(t,J=7.7Hz,1H),5.65(s,2H),2.25(s,3H) ; 13 C NMR (100MHz, CDCl 3 ):δ161.70,156.73,137.18,127.78,126.23,122.93,114.49,90.89,14.82;HRMS calcd.for C 9 H 9 O 3 [M+H] + 165.0473,found165.0545.

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Abstract

The invention provides a synthesis method of benzodioxyheterohexenone aromatic compounds, which comprises the following steps: halogenated alkane, salicylic acid or substituted salicylic acid and alkali into an organic solvent, reacting at 60-130 DEG C for 5-10 hours, and finally separating and purifying, wherein the halogenated alkane is dichloro- dibromo- or diiodo-alkane, and the mol ratio of the salicylic acid or substituted salicylic acid to the alkali is 1:(1-3). The method provided by the invention can solve the problems of narrow substrate range, rigid reaction conditions, long reaction time, multiple byproducts, low yield, need for strong acid, environment pollution and the like.

Description

【Technical field】 [0001] The invention relates to a method for synthesizing benzodioxanone aromatic compounds. 【Background technique】 [0002] Benzodioxenone aromatic compounds are a class of widely used organic synthesis intermediates. It has important application value in daily commodities, pharmaceutical production, organic synthesis, and agricultural protection. Chemists have been experimenting in recent years. Some systems have been successfully applied to this reaction, and certain research results have been obtained. However, there are many problems, such as: narrow substrate range, harsh reaction conditions, long reaction time, many by-products, low yield, need for strong acid, etc., which are not environmentally friendly and so on. [Content of the invention] [0003] The technical problem to be solved by the present invention is to provide a method for synthesizing benzodioxenone aromatic compounds, which solves the problems of narrow substrate range, harsh rea...

Claims

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Application Information

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IPC IPC(8): C07D319/08
CPCC07D319/08
Inventor 崔秀灵林锋宋秋玲高玉宇
Owner HUAQIAO UNIVERSITY
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