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The preparation method of 2-substituted-2-adamantanol compounds

An adamantanol and compound technology, applied in the field of 2-adamantanol, can solve the problems of low yield of synthesizing alkyl lithium, unsuitable for industrial production, low stability of alkyl lithium, etc., and achieves good product yield and cost Low, mild effects

Active Publication Date: 2011-12-14
四川众邦新材料股份有限公司
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  • Summary
  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the yield of synthetic alkyllithium is low. According to J.A.C.S., 63, 2480 (1941), the yield of ethyllithium is only 50% when ethyl bromide and metal lithium are used to synthesize ethyllithium
At the same time, the stability of alkyllithium is low, so the cost of using alkyllithium as an alkylating agent is relatively high
Moreover, most of the reactions using alkyllithium as an alkylating agent are carried out at low temperature (-20°C) or even ultra-low temperature (-78°C) and under anhydrous and oxygen-free conditions, which is not suitable for industrial production

Method used

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  • The preparation method of 2-substituted-2-adamantanol compounds

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Experimental program
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Effect test

Embodiment 1

[0021] Add 30 g (0.2 mol) of 2-adamantanone, 42 g (0.4 mol) of trimethyl borate, 100 ml of n-butyl ether, and 16 g (0.24 mol) of zinc powder into a 500 ml four-necked flask. Add 34 g (0.24 mol) of iodomethane. After the addition, the temperature was raised to 60°C for 4 hours, and the reaction solution was taken for gas chromatography (GC) analysis. The content of 2-adamantanone in the reaction solution was 0.3%. What is explained here is that in industrial production, the reaction time is affected by temperature, material type, etc. and cannot be refined specifically, but in batch reaction, the reaction time is usually between 3-6 hours.

[0022] Cool the reaction solution to room temperature, add 100 ml of saturated ammonium chloride aqueous solution, stir for 0.5 hours, and then let stand to separate layers. The aqueous layer is extracted three times with n-butyl ether, and the amount of n-butyl ether for each extraction is 50 ml. After three extractions, combine The organi...

Embodiment 2

[0024] Except that 26 g (0.24 mol) of bromoethane was used instead of methyl iodide, the rest of the operation was the same as in Example 1. As a result, 33.9 g of 2-ethyl-2 adamantanol was obtained with a yield of 94.2% and a GC analysis content of 99.2%.

Embodiment 3

[0026] Except that 30 g (0.24 mol) of 1-bromopropane was used instead of methyl iodide, the rest of the operation was the same as that of Example 1. As a result, 36.3 g of 2-propyl-2-adamantanol was obtained with a yield of 93.5% and a content of 99.4% by GC analysis.

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Abstract

The invention discloses a method for preparing a 2-substituted-2-adamantane alcohol compound. The method comprises the step of reacting 2-adamantanones and borates with a halogenated compound under the action of zinc powder to prepare the 2-substituted-2-adamantane alcohol compound and has the advantages of no need of air isolation, mild conditions, simple and convenient process and lower cost, and the obtained product, i.e., the 2-substituted-2-adamantane alcohols compound, can be refined through conventional methods such as water washing, concentration, filtration, recrystalization and the like and is high in yield. The method has no rigorous requirement for a solvent, preferably n-butyl ether which is beneficial to realization of high solvent recover rate and has good separation property with water, therefore, organic matters carried in wastewater are greatly reduced, and the method has a better industrial prospect.

Description

technical field [0001] The invention relates to 2-adamantanol, in particular to a preparation method of 2-substituted-2-adamantanol compounds. Background technique [0002] 2-Substituted-2-adamantanol compounds are very important fine chemical products, which can be used to prepare photoresist monomers, photochromic compounds, pharmaceutical intermediates, etc., and are used in coatings, adhesives, films , Adsorbent materials, etc. also have a wide range of uses. [0003] As a method for producing 2-substituted-2-adamantanols, it is known to use an organometallic compound to alkylate 2-adamantanone. For example, Synth. Commun., 13, 53 (1983) uses methylmagnesium bromide, and J.A.C.S., 83, 182 (1961) uses methylmagnesium iodide. [0004] However, when an organomagnesium compound or an organoaluminum compound is used as an alkylating agent for the alkylation reaction, since the reduction reaction is preferentially induced according to Tetrahedron Lett., 31, 3151 (1990), the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C35/37C07C29/38
Inventor 史翔张鸿傅绍莲牟敏
Owner 四川众邦新材料股份有限公司
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