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Preparation method of 3- careen-5-keto

A technology of carene and chromium trioxide is applied in the field of preparing 3-carene-5-one, and can solve the problem of poor selectivity of 3-carene-5-one, long reaction time, and production of 3-carene-5-one. problems such as low rate, to achieve the effect of shortening the reaction time and improving the yield

Inactive Publication Date: 2009-07-08
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But above-mentioned method shortcoming is also obvious: reaction time is long, 3-carene conversion rate is low, 3-carene-5-ketone selectivity is poor and 3-carene-5-ketone productive rate is low, therefore, need this method be improved to increase the practicability of the reaction

Method used

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  • Preparation method of 3- careen-5-keto

Examples

Experimental program
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Embodiment 1

[0017] Add 19ml of tert-butanol and 10ml of benzene into a 100ml round bottom flask, and mix evenly under the action of magnetic stirring; Weigh 10g of chromium trioxide into the round bottom flask and stir for half an hour; Pour the mixed solution into a separatory funnel for extraction, 20ml Wash the reaction bottle with benzene, the resulting bright red oil layer is the required oxidant solution, dry with magnesium sulfate, and set aside;

[0018] Add 4.1ml (3.51g, 0.026mol) 3-carene into a 250ml three-necked flask, then add the prepared oxidant solution, connect the three-necked flask with a thermometer and a glass stopper respectively; then place the three-necked flask in an ultrasonic cleaner In the water tank (ultrasonic power 100W), fill the tank with water, keep the reaction temperature in the there-necked bottle <45°C, and apply the ultrasonic wave continuously for 2 hours; stop the ultrasonic wave, slowly add 60ml (20g) oxalic acid solution within half an hour, and c...

Embodiment 2

[0022] Add 38ml of tert-butanol and 10ml of benzene into a 100ml round-bottomed flask, and mix evenly under the action of magnetic stirring; weigh 10g of chromium trioxide into the round-bottomed flask, and stir for half an hour; pour the mixed solution into a separatory funnel for extraction, 20ml Wash the reaction bottle with benzene, the resulting bright red oil layer is the required oxidant solution, dry with magnesium sulfate, and set aside;

[0023] Add 4.1ml (3.51g, 0.026mol) 3-carene into a 250ml three-necked flask, then add the prepared oxidant solution, connect the three-necked flask with a thermometer and a glass stopper respectively; then place the three-necked flask in an ultrasonic cleaner In the water tank (ultrasonic power 100W), fill the tank with water, keep the reaction temperature in the there-necked bottle <45°C, and apply the ultrasonic wave continuously for 3 hours; stop the ultrasonic wave, slowly add 60ml (20g) oxalic acid solution within half an hour, ...

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Abstract

The invention discloses a method for preparing 3-carene-5-ketone. The method comprises the following steps: a,evenly mixing tertiary butyl alcohol and benzene with volume ratio of 1.7-4.3:1, and then adding chromium trioxide solid into the mixture to stir for half an hour, and separating and extracting the mixture to prepare an oil layer which is an oxidant in the next reaction; b, mixing a raw material 3-carene and the chromium trioxide with mol ratio of 1:1.5-2.5 at a temperature of between 40 and 45 DEG C to react for 1 to 3 hours under the condition of applying 100 to 700w ultrasonic wave; and c, adding an oxalic acid solution in the reaction liquid to continue reacting for 1 hour after reaction is finished, finally extracting an organic phase by aether, washing the organic phase by 4 percent sodium bicarbonate aqueous solution to prepare an orange transparent solution, and concentrating and separating the orange transparent solution by column chromatography to prepare the target product 3-carene-5-ketone. The method shortens reaction time from 48 hours to 3 hours, and also improves conversion rate of the reactant and the yield of the target product.

Description

technical field [0001] The present invention relates to a preparation method of ketone, more specifically relates to a method for preparing 3-carene-5-ketone by using 3-carene as raw material. Background technique [0002] 3-carene is one of the main components of turpentine, and its application in organic synthesis has gradually attracted people's attention. In 1986, Arun K. Mandal et al first proposed a complete route for the synthesis of pyrethroids from 3-carene, in which the first key step is the synthesis of 3-caren-5-one from 3-carene. According to literature reports, the experiment with the highest yield of 3-carene-5-one synthesis from 3-carene so far is the experiment reported by P.H.Boyle et al. in 1971, using chromium trioxide-tert-butanol system to oxidize 3 -carene, reacted at normal temperature for 48h, the conversion rate of 3-carene was 62%, obtained 34% volatile oxidation products altogether, wherein 3-carene-5-ketone accounted for 50%, produced after colu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/627C07C45/28
Inventor 孙小玲韩文君乔俊华蔡蕍朱贤
Owner SHANGHAI INST OF TECH
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