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Preparation method of 5-chloro-1-indanone

A technology of indanone and chlorobenzene, which is 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, pollution-reducing effect

Active Publication Date: 2021-03-09
FUXIN RUIGUANG FLUORINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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

Method used

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  • Preparation method of 5-chloro-1-indanone

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Embodiment 1

[0038] In a 2000mL jacketed reactor, add 338g (3mol) of chlorobenzene and cool down to below 5°C, then add 420g (3.15mol) of aluminum trichloride and stir for 0.5h. Start to add 381 g (3 mol) of 3-chloropropionyl chloride dropwise, and complete the addition within 2 hours. After the addition, the temperature was raised to 50° C., and after 2 hours of heat preservation and reaction, the GC controlled the reaction raw materials to be ≤0.5%. Add 300g of aluminum trichloride, 90g of sodium chloride and 30g of potassium chloride to another jacketed kettle, and heat the jacketed heat transfer oil to a molten state. The reaction solution after the heat preservation was completed was added dropwise to the molten salt for 1 hour. After the dropwise addition, the temperature was raised to 130° C. for 6 hours, and the reaction was completed. Add the reaction feed liquid to 4000g of ice water for hydrolysis, control the temperature of the hydrolysis kettle to ≤50°C, stir and cool down to...

Embodiment 2

[0040]In a 2000mL jacketed reactor, add 338g (3mol) of chlorobenzene and cool down to below 5°C, then add 420g (3.15mol) of aluminum trichloride and stir for 0.5h. Start to add 381 g (3 mol) of 3-chloropropionyl chloride dropwise, and complete the addition within 2 hours. After the addition, raise the reaction temperature to 70° C., and keep the reaction for 2 hours, and control the reaction raw materials in GC to ≤0.5%. Add 600g of aluminum trichloride and 260g of sodium chloride to another jacketed kettle, heat the jacketed heat conduction oil to a molten state, add the reaction solution that has been kept warm for 1 hour, and raise the temperature to 150°C for 3 hours after the dropwise addition, and the reaction is completed. Add the reaction feed liquid to 5000g of ice water for hydrolysis, control the temperature of the hydrolysis kettle to ≤50°C, stir and cool down to below 20°C after dropping, filter, add the filter cake to the reaction kettle, add 1000g of methanol, h...

Embodiment 3

[0042] 1000mL jacketed reactor, add SiO 2 Loaded phosphotungstic acid catalyst (loading capacity 30%) 31.8g, aluminum trichloride 210g, sodium chloride 90g and potassium chloride 49g, heated to 90°C in a jacketed oil bath, kept warm for 0.5h, and controlled the temperature of the reactor at 100-110 ℃, add 190.5g (1.5mol) of 3-chloropropionyl chloride dropwise for 1.5h, after dropping, keep warm at this temperature for 30 minutes, start to add 169g (1.5mol) of chlorobenzene dropwise, take 1h, and keep warm for 4h after adding Afterwards, the GC middle control intermediate ≤ 0.5%, the reaction ends. Add the reaction feed liquid to 1250g of ice water for hydrolysis, control the temperature of the hydrolysis kettle to ≤50°C, stir and cool down to below 20°C after dropping, filter, add the filter cake into the reaction kettle, add 500g of methanol, heat to reflux, keep warm for 3h, heat Filter, wash the filter cake with chloroform heat, filter, rinse and dry, and recover the suppo...

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Abstract

The invention provides a preparation method of 5-chloro-1-indanone, and belongs to the technical field of organic synthesis. Chlorobenzene and 3-chloropropionyl chloride are used as raw materials, mixed molten salt and heteropolyacid are used as catalysts, and heating reaction is performed to obtain 5-chloro-1-ndanone, wherein the heteropolyacid is SiO2 loaded phosphotungstic acid, and the mixed molten salt is a mixture of any two or three of potassium chloride, sodium chloride and aluminum chloride. By controlling the feeding temperature and the feeding sequence, the reaction is carried out at a lower temperature, the problems of large solid amount, high temperature, violent reaction, large tar amount, carbonization of raw materials, more three wastes and the like when aluminum trichloride is used as a catalyst are avoided, and the yield of 5-chloro-1-indanone can reach up to 85%.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical and chemical intermediates, and in particular relates 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 indoxacarb (commonly known as indoxacarb), a new pesticide variety of DuPont in the United States, and also an important pharmaceutical intermediate of benzoyl indole anti-inflammatory drugs and aminoacetyl anticoagulant drugs. The synthetic route of the currently disclosed 5-chloroindanone has the following types: [0003] 1. Synthesis method using m-chlorocinnamic acid as raw material: this route uses m-chlorocinnamic acid as raw material, hydrogenates to obtain m-chlorophenylpropionic acid, chlorates to obtain m-chlorophenylpropionyl chloride, and finally cyclizes to obtain 5-chloroin...

Claims

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Application Information

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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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