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Post-treatment method of [alpha]-bromotricycle[3.3.1.13,7]decane-1-acetic acid

A technology of decane and bromination, applied in the field of preparation of α-bromotricyclo[3.3.1.13,7]decane-1-acetic acid, which can solve the problems of unfavorable recycling, low solvent utilization rate, cumbersome operation, etc. , to achieve the effect of improving solvent utilization, low toxicity and simple procedure

Inactive Publication Date: 2015-08-12
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The disadvantages of this method: 1) The yield is low, 82%, which can reach 92% after post-treatment improvement; 2) It needs to use a large amount of expensive and toxic acetonitrile as a solvent (3.82 L acetonitrile), and it is mixed with water, which is not conducive to direct recycling, and the solvent utilization rate is low; 3) The operation is cumbersome, and it needs to be distilled to obtain two phases of water and oil, and seed crystals are added. When the second batch of product is obtained, it needs to be ground. mother liquor

Method used

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  • Post-treatment method of [alpha]-bromotricycle[3.3.1.13,7]decane-1-acetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1) The completely hydrolyzed reaction solution (containing THF, water, α-bromotricyclic [3.3.1.1 3,7 ]decane-1-acetic acid) was concentrated to dryness at room temperature with a rotary evaporator at 35°C-65°C to obtain a white solid;

[0023] 2) Use ethyl acetate (EtOAc) as the solvent, heat in a 1000mL four-neck flask in a water-oil bath at 35-85°C, reflux to dissolve, use a total of 250-500mL of ethyl acetate, the solution becomes clear, cool to room temperature, add Ice-bathed overnight, crystallized, filtered, and dried to obtain 318.4 g (80%) of a white solid product;

[0024] 3) Concentrate the filtered mother liquor to dryness with a rotary evaporator at room temperature, heat it in a water-oil bath at 35-85°C, reflux to dissolve, use a total of 35-65mL of ethyl acetate, the solution becomes clear, cool to room temperature again, and place in an ice bath Overnight, crystallization gave 52.3 g (12%) of a white solid product.

Embodiment 2

[0026] 1) Put 250g of raw material 1-adamantaneacetic acid into a 3000mL four-necked flask, and after three steps, acyl chloride, bromination, and hydrolysis to obtain THF, water, α-bromotricyclic [3.3.1.1 3,7 ] The reaction solution of decane-1-acetic acid was then concentrated to dryness at room temperature with a rotary evaporator at 35-65 ° C, a white solid;

[0027] 2) Use tetrahydrofuran as the solvent, heat in a 1000mL four-neck flask in a water-oil bath at 30-80°C, and reflux to dissolve. A total of 200-450mL of solvent is used, and the solution becomes clear. After cooling to room temperature, add an ice bath overnight to crystallize. Filter and dry to obtain 270.9g (77%) of white solid product;

[0028] 3) Concentrate the filtered mother liquor to dryness with a rotary evaporator at room temperature at 35-65°C, heat in a water-oil bath at 30-80°C, and reflux to dissolve. A total of 30-70mL of solvent is used, and the solution becomes clear. Cool to room temperature a...

Embodiment 3

[0030] 1) Put 250g of raw material 1-adamantaneacetic acid into a 3000mL four-necked flask, and after three steps, acyl chloride, bromination, and hydrolysis to obtain THF, water, α-bromotricyclic [3.3.1.1 3,7 ] The reaction solution of decane-1-acetic acid was then concentrated to dryness at room temperature with a rotary evaporator at 35-65 ° C, a white solid;

[0031] 2) Use n-propyl formate as solvent, heat in a 1000mL four-neck flask in a water-oil bath at 30-95°C, and reflux to dissolve. A total of 250-500mL of solvent is used, and the solution becomes clear. After cooling to room temperature, add an ice bath overnight. Crystallization, filtration, and drying gave 274.4 g (78%) of a white solid product;

[0032] 3) Concentrate the filtered mother liquor to dryness with a rotary evaporator at room temperature at 35-65°C, heat in a water-oil bath at 30-95°C, and reflux to dissolve. A total of 30-70mL of solvent is used, and the solution becomes clear. Cool to room temperat...

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Abstract

The invention provides a post-treatment method of [alpha]-bromo-tricycle[3.3.1.13,7]decane-1-acetic acid. The method includes following steps: (1) concentrating a [alpha]-bromo-tricycle[3.3.1.13,7]decane-1-acetic acid reaction liquid prepared through a method in the prior art to form a white solid; (2) heating the white solid in a solvent to dissolve the white solid, performing cooling crystallization when the solution is clarified, and filtering and drying the solution to obtain pure [alpha]-bromo-tricycle[3.3.1.13,7]decane-1-acetic acid solid; and finally (3) concentrating the mother solution obtained through the filtration in the step (2) to obtain a solid, heating the solid to dissolve the solid, and performing cooling crystallization when the solution is clarified to obtain the pure [alpha]-bromo-tricycle[3.3.1.13,7]decane-1-acetic acid. The method is increased in yield, is reduced in waste gas, waste water and solid waste, is simplified in processes and is beneficial to industrialized production.

Description

technical field [0001] The present invention relates to α-bromotricyclic [3.3.1.1 3,7 ] The technical field of the preparation method of decane-1-acetic acid. Background technique [0002] In the patent (CN1791401), 1-adamantaneacetic acid was used as raw material to obtain the target product α-bromotricyclo [3.3.1.1 3,7 ] Decane-1-acetic acid. The hydrolysis reaction takes place in tetrahydrofuran (THF). After ensuring that the hydrolysis reaction occurs completely, for the compound α-bromotricyclo[3.3.1.1 3,7 ] The aftertreatment of decane-1-acetic acid, the method that the patent (CN1791401) takes is THF is distilled off, obtains (water and oil) two-phase mixture, then adds crystal seed, and makes reaction temperature reach room temperature, so that appear coarse . Water and acetonitrile were added, the suspension was stirred at room temperature for 2 hours, the solid was filtered and washed with acetonitrile. The filtrate contained the first crop of the desired prod...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C53/23C07C51/43
Inventor 石道权单晓燕陈旭东
Owner SHANGHAI INST OF PHARMA IND CO LTD