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Preparation method of 2-dodecyl-3-hydroxy-1,4-naphthoquinone

A technology of dodecyl and dodecylcarbenyl, which is applied in the field of preparation of bactericide intermediates, can solve the problems of high production cost, complicated operation and high palladium carbon price, and achieves low production cost, safe process and simple operation. Effect

Pending Publication Date: 2019-02-12
江苏省农用激素工程技术研究中心有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This method requires a two-step reaction to synthesize the target compound. This is because the catalytic hydrogenation of palladium carbon is not selective, so that the double bond and the carbonyl group are simultaneously reduced, so oxygen oxidation is required to obtain the target product, resulting in cumbersome operation of the method, and palladium carbon Higher prices, resulting in higher production costs

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0023] The preparation method of the 2-dodecyl-3-hydroxyl-1,4-naphthoquinone of the present embodiment is as follows:

[0024] Add 400g of methanol and 80g of 2-(1-dodecenyl)-3-hydroxy-1,4-naphthoquinone (0.235mol) into a 1L four-necked reaction flask, raise the temperature to 50°C, and control the Under the temperature, add magnesium strips in batches, add once every 30min, add 1.14g each time, add 10 times in total (total 11.4g, 0.475mol), add the last time, keep the temperature at 50°C for 2h.

[0025] After the reaction, methanol was distilled under reduced pressure until a large amount of solids were precipitated, and the temperature did not exceed 60°C. After the distillation was completed, an appropriate amount of water was added, and the temperature was lowered to below 10°C. After stirring for 30 minutes, the product precipitated, and was filtered by suction to obtain 76.4 g of 2-dodecyl-3-hydroxy-1,4-naphthoquinone with a yield of 94.9% and a purity of 97.6% (HPLC). ...

Embodiment 2～ Embodiment 5）

[0027] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.

[0028] Table 1

[0029]

Embodiment 6～ Embodiment 9）

[0031] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 2.

[0032] Table 2

[0033]

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PUM

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Abstract

The invention discloses a preparation method of 2-dodecyl-3-hydroxy-1,4-naphthoquinone. The 2-dodecyl-3-hydroxy-1,4-naphthoquinone is obtained by one-step reduction reaction of 2-(1-dodecanecarbenyl)-3-hydroxy-1,4-naphthoquinone, and the one-step reduction reaction is carried out in the presence of magnesium ribbons and methanol, wherein the molar ratio of the 2-(1-dodecanecarbenyl)-3-hydroxy-1,4-naphthoquinone to the magnesium ribbons is (1:1)-(1:3), the weight ratio of the 2-(1-dodecanecarbenyl)-3-hydroxy-1,4-naphthoquinone to the methanol is (1:3)-(1:10), the temperature of the one-step reduction reaction is 25-70 DEG C, and the time of the one-step reduction reaction is 1-5h. The preparation method disclosed by the invention adopts a reduction system containing the magnesium ribbons and methanol to reduce the 2-(1-dodecanecarbenyl)-3-hydroxy-1,4-naphthoquinone to prepare the 2-dodecyl-3-hydroxy-1,4-naphthoquinone, and the reduction system can selectively hydrogenate double bonds under certain conditions, so that a target product can be obtained by only one-step reaction.

Description

technical field [0001] The invention belongs to the technical field of preparation of bactericide intermediates, and in particular relates to a preparation method of 2-dodecyl-3-hydroxyl-1,4-naphthoquinone, an intermediate of acequinone. Background technique [0002] The chemical name of acequinone is 2-(acetoxy)-3-dodecyl-1,4-naphthoquinone. It is a kind of contact acaricide without systemic activity. It is used in fruit trees such as pears , peaches, citrus, cucumbers, vegetables, and grapes to prevent and control mite hazards, the dose is 0.56-2.24kg / ka. [0003] 2-dodecyl-3-hydroxyl-1,4-naphthoquinone is an important intermediate for the synthesis of acequinone. For the preparation of this intermediate, U.S. Patent Document US5225578A discloses a 2-(1-decaquinone Dialkylcarbenyl)-3-hydroxy-1,4-naphthoquinone as the starting material, first hydrogenated by palladium carbon to obtain 2-dodecyl-1,3,4-trihydroxynaphthalene, and then oxidized to obtain 2 - dodecyl-3-hydroxy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C46/00C07C50/32
CPCC07C46/00C07C2602/28C07C50/32
Inventor 刘晓佳孙永辉邹佩佩孔繁蕾
Owner 江苏省农用激素工程技术研究中心有限公司