A kind of preparation method of 5-chloro-1-indanone

A technology of indanone and chlorobenzene, applied in the field of preparation of 5-chloro-1-indanone, can solve the problems of easy blockage of exhaust pipes, large amount of aluminum trichloride and high reaction temperature, and achieves simple process and equipment requirements Low and pollution-reducing effect

Active Publication Date: 2022-06-14
FUXIN RUIGUANG FLUORINE CHEM
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  • Abstract
  • Description
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Problems solved by technology

Both the one-pot method and the step-by-step method have the same problems. The reaction temperature is high (150-200 ° C), the amount of aluminum trichloride is large, the amount of tar is large, and the sublimated aluminum trichloride and product solids are easy to block the discharge. gas pipeline, causing potential safety hazards, low yield (50-70%), poor product color

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  • A kind of preparation method of 5-chloro-1-indanone

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Embodiment 1

[0038] In a 2000 mL jacketed reaction kettle, 338 g (3 mol) of chlorobenzene was added, and the temperature was lowered to below 5 °C, and then 420 g (3.15 mol) of aluminum trichloride was added and stirred for 0.5 h. The dropwise addition of 381 g (3 mol) of 3-chloropropionyl chloride was started, and the addition was completed within 2 h. After the addition is completed, the temperature is raised to 50° C., and after the reaction is incubated for 2 hours, the reaction raw materials are controlled in GC to be ≤0.5%. Another jacketed kettle was added with 300 g of aluminum trichloride, 90 g of sodium chloride and 30 g of potassium chloride, and the jacketed heat-conducting oil was heated to a molten state. The reaction at the end of the heat preservation was added dropwise to the molten salt for 1 hour. After the dropwise addition, the temperature was increased to 130° C. for 6 hours, and the reaction was completed. The reaction liquid was added to 4000g ice water for hydroly...

Embodiment 2

[0040]In a 2000 mL jacketed reaction kettle, 338 g (3 mol) of chlorobenzene was added, and the temperature was lowered to below 5 °C, then 420 g (3.15 mol) of aluminum trichloride was added, and the mixture was stirred for 0.5 h. The dropwise addition of 381 g (3 mol) of 3-chloropropionyl chloride was started, and the addition was completed within 2 h. After the addition is completed, the reaction temperature is raised to 70° C., and after the reaction is incubated for 2 hours, the reaction raw materials in the GC are controlled to be less than or equal to 0.5%. Add 600 g of aluminum trichloride and 260 g of sodium chloride to another jacketed kettle, heat the jacketed heat-conducting oil to a molten state, and dropwise add the reaction solution that has been kept warm for 1 hour. Add the reaction liquid into 5000g ice water for hydrolysis, control the temperature of the hydrolysis kettle to be less than or equal to 50°C, drop the temperature to below 20°C with stirring, filte...

Embodiment 3

[0042] 1000mL jacketed reactor, add SiO 2 Loaded phosphotungstic acid catalyst (loaded 30%) 31.8g, aluminum trichloride 210g, sodium chloride 90g and potassium chloride 49g, the jacketed oil bath was heated to 90°C, kept for 0.5h, and the temperature of the reaction kettle was controlled to 100-110 ℃, 190.5g (1.5mol) of 3-chloropropionyl chloride was added dropwise for 1.5h, the dropping was completed, the temperature was kept for 30 minutes, and 169g (1.5mol) of chlorobenzene was added dropwise for 1h, and the incubation reaction was completed for 4h After that, the GC intermediate control intermediate≤0.5% reaction was completed. Add the reaction liquid into 1250g ice water for hydrolysis, control the temperature of the hydrolysis kettle to be less than or equal to 50°C, drop the temperature to below 20°C with stirring, filter, add the filter cake to the reaction kettle, add 500g methanol, heat to reflux, keep for 3h, heat Filtration, the filter cake was washed with chlorof...

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Abstract

The invention provides a preparation method of 5-chloro-1-indanone, which belongs to the technical field of organic synthesis. Taking chlorobenzene and 3-chloropropionyl chloride as raw materials, using mixed molten salt and heteropolyacid as a catalyst, and heating up to react to obtain 5-chloro-1-indanone; the heteropolyacid is SiO 2 Loading phosphotungstic acid, the mixed molten salt is a mixture of any two or three of potassium chloride, sodium chloride and aluminum chloride. In the present invention, by controlling the feeding temperature and feeding sequence, the reaction is carried out at a relatively low temperature, avoiding the problems of using aluminum trichloride as a catalyst with a large amount of solids, high temperature, violent reaction, large amount of tar, carbonization of raw materials, and more three wastes. , the yield of 5-chloro-1-indanone can be as high as 85%.

Description

technical field [0001] The invention belongs to the technical field of synthesis in pharmaceutical chemical intermediates, in particular to a preparation method of 5-chloro-1-indanone. Background technique [0002] 5-Chloro-1-indanone, referred to as 5-chloroindanone, molecular formula C 9 H 7 OCl, molecular weight 166.61, CAS 42348-86-7. It is an important intermediate of DuPont's new pesticide variety indoxacarb (common name is indoxacarb), and also an important pharmaceutical intermediate of benzoyl indole anti-inflammatory drugs and aminoacetyl anticoagulants. The synthetic route of 5-chlorindanone disclosed at present has the following several: [0003] 1, the synthetic method that takes m-chlorocinnamic acid as raw material: this route takes m-chlorocinnamic acid as raw material, obtains m-chlorophenylpropionic acid through hydrogenation, chlorination obtains m-chlorophenylpropionyl chloride, and finally cyclization obtains 5-chloroindene ketone. The main disadvan...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/697C07C45/45
CPCC07C45/455C07C49/697Y02P20/584
Inventor 孙立芹张洪学姜殿宝
Owner FUXIN RUIGUANG FLUORINE CHEM
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