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Method for synthesizing cycloheptatriene

A technology of cycloheptatriene and a synthesis method is applied in the fields of pharmaceutical intermediates, medicines, chemical intermediates and pesticides, and can solve the problems of high toxicity of synthetic raw material diazomethane, unsuitable for large-scale industrial production, unsuitable for industrialized production and the like , to achieve the effect of ensuring safety, low toxicity and saving reaction time

Inactive Publication Date: 2010-10-13
NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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Problems solved by technology

[0007] The above-mentioned preparation method not only has a low total yield, but also has the disadvantages that the synthetic raw material diazomethane used is highly toxic and unstable, which will seriously affect the health of operators and cause environmental pollution. Therefore, it is not suitable for industrial production.
[0008] M.E.Winberg reported the synthesis of cycloheptatriene (J.Org.Chem.1959, 24, 246) by using 7,7 dichlorobicyclo[4.1.0]heptane at a high temperature of 490°C (J.Org.Chem.1959, 24, 246). It can only be completed under high pressure, the reaction conditions are harsh, it is not suitable for large-scale industrial production, and there are potential safety hazards, and the yield of the target product is only about 30%, which is not very ideal

Method used

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  • Method for synthesizing cycloheptatriene
  • Method for synthesizing cycloheptatriene
  • Method for synthesizing cycloheptatriene

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Add 165 grams (1.0mol) 7,7-dichlorobicyclo[4.1.0] heptane in 1000 milliliters one-mouth bottle, 400g (3.7mol) diethylene glycol (molecular weight is 106 polyethylene glycols), 20 grams (0.2 mol) of cuprous chloride was stirred and reacted at 140° C. for 8 hours. Then above-mentioned reaction mixture is cooled to normal temperature, adds 300 milliliters of methanol, distills out the azeotrope (cut) of methanol and cycloheptatriene at 80 ℃, transfers azeotrope in the separatory funnel, adds 200 milliliters of water, then Extracted twice with 150 ml of ether, combined the ether layers, dried, and distilled off the ether under reduced pressure to obtain 45 g of oily liquid cycloheptatriene. Yield 50%.

Embodiment 2

[0029] Add 165 grams (1.0mol) of 7,7-dichlorobicyclo[4.1.0]heptane, 500 grams of PEG600 (0.83mol), 15 grams (0.1mol) of cuprous bromide in a 1000 milliliter single-necked bottle, and stir at 140°C React for 8 hours. Cool to normal temperature, add 300 ml of methanol, distill out the azeotrope of methanol and cycloheptatriene at 80°C, transfer the azeotrope to a separatory funnel, add 200 ml of water, extract twice with 200 ml of ether, combine the ether layers, and dry , Diethyl ether was distilled off under reduced pressure to obtain 28 grams of oily liquid cycloheptatriene. Yield 32%.

Embodiment 3

[0031] Add 165 grams (1.0mol) of 7,7-dichlorobicyclo[4.1.0]heptane, 500 grams of PEG2000 (0.25mol), 15 grams (0.1mol) of cuprous bromide in a 2000 milliliter single-necked bottle, and stir at 140°C React for 10 hours. Cool to normal temperature, add 500 ml of methanol, distill out the azeotrope of methanol and cycloheptatriene at 80°C, transfer the azeotrope to a separatory funnel, add 400 ml of water, extract twice with 300 ml of ether, combine the ether layers, and dry , Diethyl ether was distilled off under reduced pressure to obtain 42 g of oily liquid cycloheptatriene. Yield 46.7%.

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Abstract

The invention discloses a method for synthesizing cycloheptatriene, which comprises the following preparation steps of: adding 7,7-dichloro-bicyclo [4.1.0] heptane, an organic solvent and a copper salt catalyst into a reaction vessel and reacting for 2-10 hours at the temperature of 110-180 DEG C; and then, cooling a reaction mixture to normal temperature, adding an entrainer which can form an azeotrope with the generated cycloheptatriene into the reaction mixture, then distilling out the azeotrope formed by the cycloheptatriene and the entrainer at normal pressure, afterwards adding water into the azeotrope, then adding diethyl ether for extraction, extracting the obtained diethyl ether layer, drying, afterwards decompressing and distilling off the diethyl ether so as to obtain the cycloheptatriene. The method for synthesizing the cycloheptatriene has the advantages of mild reaction condition, short reaction route, short reaction period, simple postprocessing, high product yield, no use of raw materials with large toxicity, such as diazomethane and the like, better safety and environmental protection and is suitable for industrialized production.

Description

technical field [0001] The invention relates to the fields of medicine, pesticide, chemical intermediate and pharmaceutical intermediate, and mainly relates to a synthesis method of cycloheptatriene. technical background [0002] Cycloheptatriene is an important chemical intermediate, such as being widely used in organometallic ligands, and preparing chemical products such as cycloheptatriene nitrile and cycloheptatriene amine. At present, there are generally several preparation methods for cycloheptatriene as follows. Wherein, the earliest is the synthetic method (Ber., 1911,44,3432) process route invented by R.Willstatter as follows: [0003] [0004] From the above-mentioned process route, it is not difficult to see that this route uses cycloheptanone as a raw material, and the target product is finally synthesized after 12 steps. Therefore, there is a long reaction route, which prolongs the reaction cycle and causes low yield. Complicated and incapable of industrial...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/24C07C1/26
Inventor 张华星骆成才杨志杰赵文娜
Owner NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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