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Process for producing 2-alkyl-2-adamantyl ester

A technology of adamantyl ester and adamantyl alkoxylithium, which is applied in the field of preparation of 2-alkyl-2-adamantyl ester, can solve the problems of difficult refining and low yield, and achieve simple refining and improved Yield, effect of simple preparation

Inactive Publication Date: 2003-07-09
TOKUYAMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the preparation method of above-mentioned existing 2-alkyl-2-adamantyl ester has a big problem in industry from low yield and difficult refining.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] In a 500ml 4-neck flask equipped with a stirring blade, a thermometer, a condenser, and a dropping funnel, 30g of tetrahydrofuran and 2.78g (0.4mol) of lithium metal were added under a nitrogen atmosphere. In this solution, under a nitrogen atmosphere, the reaction temperature was controlled at about 40°C, and a solution of 30 g (0.2 mol) of 2-adamantanone (0.2 mol) and 26.2 g (0.24 mol) of ethyl bromide previously dissolved in 90 g of tetrahydrofuran was added dropwise. . After the dropwise addition, the temperature was raised to 45° C., and reaction aging was carried out for 1 hour.

[0072] After visually confirming the disappearance of metallic lithium, 4.36 g (0.04 mol) of ethyl bromide was added, followed by stirring at 45° C. for 1 hour to prepare a lithium 2-ethyl-2-adamantyl alkoxide solution. Analysis by gas chromatography (GC) confirmed that the conversion rate of 2-adamantanone at this time was 98%.

[0073] Replace the 500ml 4-neck flask with stirring bla...

Embodiment 2

[0077]In a 500ml 4-neck flask equipped with a stirring blade, a thermometer, a condenser, and a dropping funnel, 30g (0.2mol) of 2-adamantanone (0.2mol) and 26.2g (0.24mol) of ethyl bromide were dissolved in 120g of tetrahydrofuran under a nitrogen atmosphere. middle. Under a nitrogen atmosphere, the reaction temperature was controlled at about 40° C., and 2.78 g (0.4 mol) of lithium metal was added to the solution in five portions (0.5 g each time for the first four times, and 0.78 g for the last time). After the dropwise addition, the temperature was raised to 45° C., and reaction aging was carried out for 1 hour.

[0078] After visually confirming the disappearance of metallic lithium, 4.36 g (0.04 mol) of ethyl bromide was added, followed by stirring at 45° C. for 1 hour to prepare a lithium 2-ethyl-2-adamantyl alkoxide solution. Analysis by gas chromatography (GC) confirmed that the conversion rate of 2-adamantanone at this time was 93%.

[0079] Thereafter, the treatme...

Embodiment 3

[0082] According to the operation of Example 1, a solution of lithium 2-ethyl-2-adamantyl alkoxide was prepared. Analysis by gas chromatography (GC) confirmed that the conversion rate of 2-adamantanone at this time was 98%.

[0083] In the aforementioned solution obtained, 0.08 g (0.4 mmol) of phenothiazine was added as a polymerization inhibitor, and under a nitrogen atmosphere, the reaction temperature was cooled below 10° C., and 22.0 g (0.21 mol) of methacryloyl chloride was added dropwise thereto. ), and finished dripping in 2 hours. After completion of the dropwise addition, the mixture was stirred at 10° C. or lower for 4 hours to mature the reaction.

[0084] After reaction aging, 10 g of methanol and 16 g of a 10% by mass sodium hydroxide aqueous solution were added to the obtained reaction liquid while keeping the temperature below 10° C., and the organic layer was separated after stirring for 1 hour. After further washing the organic layer with a 10% by mass aqueo...

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PUM

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Abstract

A process for producing a 2-alkyl-2-adamantyl ester, characterized by mixing and reacting a solution or suspension containing 2-adamantanone and a halogenoalkyl compound with lithium metal to obtain a lithium 2-alkyl-2-adamantyl alcoholate and subsequently reacting the lithium 2-alkyl-2-adamantyl alcoholate with an acid halide.

Description

technical field [0001] The present invention relates to 2-alkyl-2-adamantyl acrylate and 2-alkyl-2-adamantyl methacrylate (hereinafter referred to as 2-alkyl-2- A method for producing 2-alkyl-2-adamantyl esters such as adamantyl (meth)acrylate). Background technique [0002] It is known that a resist prepared from 2-alkyl-2-adamantyl ester as a raw material has high resistance to dry etching in a semiconductor manufacturing process (for example, Japanese Patent Laid-Open No. 5-265212). The prospect of the drug is concerned. [0003] As a method for producing 2-alkyl-2-adamantyl esters, it is known to use an alkylating agent composed of an organometallic compound to alkylate 2-adamantanone, and then convert the obtained 2-alkyl - A method of esterifying a 2-adamantyl metal alkoxide with an acid halide (JP-A-10-182552, etc.). [0004] In the alkylation reaction in the preceding stage of the above reaction, when the alkylation reaction is carried out using an organomagnesium...

Claims

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Application Information

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IPC IPC(8): C07C29/68C07C67/14
CPCC07C2103/74C07C67/14C07C29/68C12C11/02C07C2603/74C07C35/46C07C69/54
Inventor 山口真男菊地秀树广田吉洋
Owner TOKUYAMA CORP
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