Preparation method for 1-benzosuberone

A technology of benzocycloheptanone and catalyst, applied in the field of preparation of 1-benzocycloheptanone, can solve problems such as unfavorable environment, difficulty in obtaining benzobicyclic hydrocarbon compounds, harsh reaction conditions, etc., and achieves shortened process route, The effect of wide source of raw materials and short process route

Inactive Publication Date: 2017-04-05
SICHUAN TONGSHENG BIOTECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] 2) The document J.Org.Chem.1973,38(8),1445-1450 reported that benzene and glutaric anhydride were used as raw materials, prepared by Friedel-Crafts acylation reaction, Claisen reduction and acid chloride, Friedel-Crafts acylation Ring and other four-step reactions to prepare 1-benzocycloheptanone; the reaction steps are longer, and metal zinc-mercury is used as a reducing agent in the process, and the fourth step uses carbon disulfide as a reaction solvent, which is unfavorable to the environment and unfavorable for industrialization; process The route is as follows:
[0007] 3) Document Helvetica Chimica Acta; 1998,81(2), 251-267 reported that 1-benzocycloheptanone was obtained by rearrangement of benzobicyclic hydrocarbon compound, with a yield of 97%; but the benzobicyclic hydrocarbon compound Difficult to obtain, literature

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  • Preparation method for 1-benzosuberone
  • Preparation method for 1-benzosuberone
  • Preparation method for 1-benzosuberone

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Experimental program
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Effect test

Embodiment 1

[0037] The preparation method of 1-benzocycloheptanone is as follows:

[0038]Add 332.3g of delta-valerolactone and 2.33L of benzene in a 5L three-necked flask equipped with a thermometer, mechanical stirring, reflux pipe, and tail gas receiving device, start stirring, add 1.77kg of anhydrous aluminum trichloride in batches at room temperature, and control it at Complete the addition within 2 hours, heat the reaction system until the reflux reaction temperature is controlled at 80°C, and the reaction time is controlled at 14 hours. TLC detects that the δ-valerolactone reaction is complete, stop the reaction, cool to room temperature, and slowly pour the reaction system into 8kg crushed ice cubes and 1.4L of concentrated hydrochloric acid mixture, stirring, liquid separation. The aqueous phase was extracted once with 2L of toluene; the organic phases were combined, and the organic phase was washed with 10% NaOH solution and 1L of water successively, dried with sodium sulfate, f...

Embodiment 2

[0041] The preparation method of 1-benzocycloheptanone is as follows:

[0042] Add 332.3g of δ-valerolactone and 2.99L of benzene in a 5L three-necked flask equipped with a thermometer, mechanical stirring, reflux pipe, and tail gas receiving device, start stirring, add 1.892kg of anhydrous titanium tetrachloride in batches at room temperature, and control it at Complete the addition within 2 hours, heat the reaction system until the reflux reaction temperature is controlled at 90°C, and the reaction time is controlled at 16 hours. TLC detects that the δ-valerolactone reaction is complete, stop the reaction, cool to room temperature, and slowly pour the reaction system into 8kg crushed ice cubes and 1.4L of concentrated hydrochloric acid mixture, stirring, liquid separation. The aqueous phase was extracted once with 2L of ethyl acetate; the organic phases were combined, and the organic phase was washed with 10% KOH solution and 1L of water successively, dried with sodium sulfa...

Embodiment 3

[0044] The preparation method of 1-benzocycloheptanone is as follows:

[0045] Add 16.6g of δ-valerolactone and 132mL of benzene into a 250mL three-neck flask equipped with a thermometer, mechanical stirring, reflux tube, and tail gas receiving device, start stirring, add 83.9g of anhydrous aluminum trichloride in batches at room temperature, and control it within 30min Addition is complete; heat the reaction system to reflux, control the reaction at 85°C, and control the reaction time at 12h. TLC detects that the δ-valerolactone has completely reacted, stop the reaction, and cool to room temperature; slowly pour the reaction system into 400g crushed ice cubes and 70mL In a mixture of concentrated hydrochloric acid, stir and separate the liquids. The aqueous phase was extracted once with 200 mL of methyl tert-butyl ether; the organic phases were combined, and the organic phase was washed with 10% sodium carbonate solution and 200 mL of water successively, dried with sodium sul...

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Abstract

The invention provides a preparation method for 1-benzosuberone. The preparation method for the 1-benzosuberone includes the following steps that (A) a catalytic reaction is performed through a Lewis acid catalyst by taking delta-valerolactone and benzene as raw materials, the reaction temperature is controlled to be 80-90 DEG C, and the reaction time is controlled to be 12-16 h; and (B) after a quenching reaction, an organic phase is obtained through extraction, the organic phase is subjected to impurity removing and concentration treatment, and then the 1-benzosuberone is obtained. The preparation method for the 1-benzosuberone has the effects that the reaction route is short, operation is easy, the raw materials are easy to obtain, and the product is high in yield and purity.

Description

technical field [0001] The invention relates to the field of pharmacy, in particular to a preparation method of 1-benzocycloheptanone. Background technique [0002] 1-Benzoheptanone and its similar structure benzocyclones contain α,β-unsaturated cyclic ketone structure, so they have a wide range of biological activities such as anticancer, antibacterial, antiviral, antihypertensive, and regulating plant growth. , it is an important pharmaceutical and fine chemical intermediate, which can be used to prepare 2-aminothiazole and its amide derivatives, and can also be used to construct organic synthesis building blocks such as α-allyl ketones and β-amino ketones. Piece. [0003] The 1-benzocycloheptanone synthesis method reported in the current literature mainly contains the following three kinds: 1) The literature "Fine Chemical Industry" 2010, 27, 929-932 reported that benzene and glutaric anhydride were used as raw materials, through Friedel-Crafts acylation reaction , Wolf...

Claims

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Application Information

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IPC IPC(8): C07C49/67C07C45/60
CPCC07C45/60C07C49/67
Inventor 黄青春陈纹锐伍万兵张丽白顺强
Owner SICHUAN TONGSHENG BIOTECH
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