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Synthesis method of 3-[4-(methyl sulfonyl)-2-chlorobenzoyl]bicyclo[3.2.1]-2.4-octanedione

A technology of methylsulfonyl and chlorobenzoyl, which is applied to the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of hydroxyl compounds. Less, less environmental pollution, high yield effect

Inactive Publication Date: 2016-06-22
JIANGSU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods either have high raw material prices or many synthesis steps, so these methods seem uneconomical

Method used

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  • Synthesis method of 3-[4-(methyl sulfonyl)-2-chlorobenzoyl]bicyclo[3.2.1]-2.4-octanedione
  • Synthesis method of 3-[4-(methyl sulfonyl)-2-chlorobenzoyl]bicyclo[3.2.1]-2.4-octanedione
  • Synthesis method of 3-[4-(methyl sulfonyl)-2-chlorobenzoyl]bicyclo[3.2.1]-2.4-octanedione

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Embodiment 1

[0041] 1. Synthesis of 3,4-dichlorobicyclo[3.2.1]-2-octene

[0042]

[0043] Dissolve 80.0g (0.848mol) of norbornene in 406.8g (3.408mol) of chloroform and 8mL of ethanol, add 1.6g (0.0084mol) of benzyltrimethylammonium chloride, heat to 50°C, and add dropwise under electric stirring 272 g (3.4 mol) of 50% aqueous sodium hydroxide solution was added. After the addition, the mixture was stirred and reacted at 50° C. for 3 hours, and the reaction progress was detected by TLC (developing agent: petroleum ether). The mixture was poured into 300 g of ice water and extracted with ethyl acetate (400 mL×2). The organic layer was washed once with 300 mL of water, dried over anhydrous sodium sulfate, and concentrated to dryness. 122 g of an oily product was obtained with a yield of 81.2%. The next reaction was carried on without further purification. 1 H-NMR (400MHz, CDCl 3 ,δ / ppm):6.14(d,J=7.2Hz,1H,=CH),4.22(d,J=2.8Hz,1H,CHCl),2.74~2.62(m,2H,CH 2 ),2.07~1.95(m,2H,CH 2 ),1.73~1...

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Abstract

3-[4-(Methylsulfonyl)-2-chlorobenzoyl]bicyclo[3.2.1]-octane-2,4-dione is an intermediate for synthesizing rice field herbicides. The invention discloses a A method for synthesizing 3-[4-(methylsulfonyl)-2-chlorobenzoyl]bicyclo[3.2.1]-octane-2,4-dione, comprising the following steps: taking norbornene as a raw material, After the addition and ring expansion reaction of dichlorocarbene, the hydrolysis reaction generates 3-chlorobicyclo[3.2.1]-3-octen-2-ol; then oxidizes allyl alcohol to obtain α,β-unsaturated ketone; Then react with sodium hydroxide under the action of a catalyst to obtain bicyclo[3.2.1]octane-2,4-dione, and finally undergo acylation reaction to obtain the target product. The raw materials and reagents used are cheap and easy to obtain, the synthesis method is simple and the reaction conditions are mild.

Description

technical field [0001] The invention relates to a synthesis method of 3-[4-(methylsulfonyl)-2-chlorobenzoyl]bicyclo[3.2.1]-2,4-octanedione, which belongs to the fields of chemical industry and chemical medicine. Background technique [0002] 2-substituted benzoyl-1,3-cyclohexanedione compounds have certain herbicidal activity (US5006158, CN85109770), 3-(hydrocarbylthio)-2-benzoylcyclohex-2-one and substituted aromatic Bicyclic diketones can be used as herbicidally active compounds (US4762551, EP0338992). However, these compounds are highly phytotoxic to rice, and they are difficult to use as herbicides in rice fields. Compared with the herbicidal activity of the above-mentioned diketone compounds, the substituted benzoylcycloenone 1 has quite high herbicidal activity on annual and perennial weeds growing in rice fields, while showing very low activity on rice plants. Phytotoxicity (CN1105023A), good mobility and water solubility in soil (CN1105023A, JP10109972A, AU672058B2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/24
CPCC07C315/04C07C17/32C07C29/124C07C45/29C07C45/298C07C45/67C07C317/24C07C49/443C07C49/693C07C35/52C07C23/32
Inventor 王雅珍郑纯智林伟
Owner JIANGSU UNIV OF TECH
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