The synthetic method of 1-hydroxyl-3-hydroxymethyladamantane

A technology of hydroxymethyladamantane and synthesis method, which is applied in the field of synthesis of 1-hydroxy-3-hydroxymethyladamantane, can solve the problems of product purification increase, difficulty, low conversion rate, etc., and achieve reduction of reaction impurities and by-products Reaction, improve industrial production, and improve the effect of yield

Active Publication Date: 2015-12-09
XUZHOU B&C CHEM CO LTD
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Problems solved by technology

[0006] In this technology, sodium borohydride is directly used as the reducing agent. The efficiency of sodium borohydride to reduce carboxylic acid is not high, the conversion rate is very low, the reaction temperature is relatively high, and the reaction of raw materials is not complete, which increases the difficulty of product purification.

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  • The synthetic method of 1-hydroxyl-3-hydroxymethyladamantane

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Embodiment 1

[0022] The steps of the synthetic method of 1-hydroxy-3-hydroxymethyladamantane in the present invention are as follows:

[0023] 1) First prepare 2% potassium hydroxide aqueous solution, add 40g potassium permanganate to the potassium hydroxide aqueous solution at room temperature, then add 1-adamantanecarboxylic acid in batches, the added amount is 40g (0.22mol) ), slowly warming the above reaction solution to 70-85°C until the reaction solution turns brown, then cooling the reaction solution to 20-30°C; adding concentrated hydrochloric acid at room temperature, and adjusting the reaction solution to be strongly acidic. The solid sodium bisulfite was then added until the solid manganese dioxide reaction was complete. The white precipitate was collected by filtration, washed three times with water, and dried in vacuo to obtain 36.2 g of crude 1-hydroxy-3-adamantanecarboxylic acid with a yield of 83.1%. m.p.198-199", the crude product was recrystallized from acetone:water (9:...

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Abstract

The invention discloses a synthetic method of 1-hydroxyl-3-hydroxymethyl adamantine. The synthetic method comprises the following steps of: 1) preparing an alkaline aqueous solution, and then adding potassium permanganate; adding 1-adamantine in batches to obtain a reaction solution; heating up the reaction solution slowly till the reaction solution becomes brown, and then cooling the reaction solution; adding concentrated acid in room temperature, and mixing the reaction solution to be highly acid; and adding sodium hydrogen sulfite solids, after washing the filtrated white precipitation with water, and vacuumizing to obtain a crude product 1-hydroxyl-3-adamantanecarboxylic acid; and 2) reacting sodium borohydride and zinc chloride in tetrahydrofuran (THF) to generate zinc borohydride, and then dissolving the crude product 1-hydroxyl-3-adamantanecarboxylic acid into the THF, and concentrating to obtain the final product through some steps. According to the invention, a bran-new synthetic method is adopted, so that the yield of the product is improved by the steps of temperature control and aftertreatment in the method.

Description

technical field [0001] The present invention relates to a method for synthesizing adamantane, and more particularly, the present invention relates to a method for synthesizing 1-hydroxy-3-hydroxymethyladamantane. Background technique [0002] The structure of 1-hydroxy-3-hydroxymethyladamantane is as follows: [0003] [0004] At present, the commonly used method for synthesizing 1-hydroxy-3-hydroxymethyladamantane is as follows: adding 1-adamantanecarboxylic acid to the potassium permanganate aqueous solution in batches to obtain a reaction solution, heating up the reaction, and then adding the temperature at room temperature. Concentrated acid, the reaction solution was adjusted to strong acid, then sodium bisulfite solid was added, after filtration, the white precipitate was washed with water, and then dried in vacuo to obtain crude 1-hydroxy-3-adamantanecarboxylic acid; [0005] Add sodium borohydride to THF, then slowly add 1-hydroxy-3-adamantanecarboxylic acid to t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C35/37C07C29/147
Inventor 贺宝元尹志清陈宣锦李兆吉彭剑平潘笑娟宋宝发朱华君李捷
Owner XUZHOU B&C CHEM CO LTD
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