JP2013028559A5

JP2013028559A5 -

Info

Publication number: JP2013028559A5
Application number: JP2011165361A
Authority: JP
Filing date: 2011-07-28
Publication date: 2014-09-04

Description

すなわち、本発明は、下記式（２）で表わされる3-クロロ-4-メチル安息香酸クロライドにイソプロピルアルコールを反応させ、下記式（１）で表わされる3-クロロ-4-メチル安息香酸イソプロピルを製造するに際し、
前記イソプロピルアルコールを前記3-クロロ-4-メチル安息香酸クロライドの０．９〜１．２倍モルの割合で使用し、また、
前記イソプロピルアルコールを前記3-クロロ-4-メチル安息香酸クロライド中に無溶媒及び反応温度６０〜１４０℃の条件下に撹拌しながら滴下して反応させ、
得られた反応生成物を分離精製し、下記式（１）で表わされる3-クロロ-4-メチル安息香酸イソプロピルを得ることを特徴とする3-クロロ-4-メチル安息香酸イソプロピルの製造方法である。 That is, the present invention may be prepared by reacting isopropyl alcohol 3-chloro-4-methylbenzoic acid chloride represented by the following formula (2), 3-chloro-4-methylbenzoic acid isopropyl represented by the following formula (1) In manufacturing,
The isopropyl alcohol is used in a proportion of 0.9 to 1.2 moles of the 3-chloro-4-methylbenzoic acid chloride, and
The isopropyl alcohol is reacted dropwise with stirring in the 3-chloro-4-methylbenzoic acid chloride under conditions of no solvent and a reaction temperature of 60 to 140 ° C. ,
The reaction product obtained was separated and purified production method of the following formula (1) to give the represented 3-chloro-4-methylbenzoic acid isopropyl in characterized Rukoto 3-chloro-4-methylbenzoic acid isopropyl It is.

また、本発明は、下記式（３）で表わされる4-メチル安息香酸クロライドを塩素及びルイス酸触媒の存在下に核塩素化し、得られた前記式（２）で表わされる3-クロロ-4-メチル安息香酸クロライドにイソプロピルアルコールを反応させ、前記式（１）で表わされる3-クロロ-4-メチル安息香酸イソプロピルを製造するに際し、
前記核塩素化反応においては、ルイス酸触媒として塩化第二鉄を０．１〜１．０重量%の割合で使用すると共に、無溶媒及び塩素導入量０．５倍モル以上の条件下に反応させ、また、
反応終点の塩素化度を０．８８〜０．９１の範囲に制御すると共に、反応終了後には反応容器内を速やかに窒素置換し、更に、
前記エステル化反応においては、前記イソプロピルアルコールを前記3-クロロ-4-メチル安息香酸クロライドの０．９〜１．２倍モルの割合で使用すると共に、前記イソプロピルアルコールを前記3-クロロ-4-メチル安息香酸クロライド中に無溶媒及び反応温度６０〜１４０℃の条件下に撹拌しながら滴下して反応させ、
次いで得られた反応生成物を分離精製し、前記式（１）で表わされる3-クロロ-4-メチル安息香酸イソプロピルを得ることを特徴とする3-クロロ-4-メチル安息香酸イソプロピルの製造方法である。 In addition , the present invention provides 4-chlorobenzoic acid chloride represented by the above formula (2) obtained by nucleating 4-methylbenzoic acid chloride represented by the following formula (3) in the presence of chlorine and a Lewis acid catalyst. - upon reacted with isopropyl alcohol methylbenzoic acid chloride, to produce a 3-chloro-4-methylbenzoic acid isopropyl represented by the formula (1),
In the nuclear chlorination reaction, ferric chloride is used as a Lewis acid catalyst in a proportion of 0.1 to 1.0% by weight, and the reaction is carried out under conditions of no solvent and a chlorine introduction amount of 0.5 times mol or more. And also
The degree of chlorination at the end of the reaction is controlled to be in the range of 0.88 to 0.91, and the reaction vessel is immediately purged with nitrogen after the completion of the reaction.
In the esterification reaction, as well as using the isopropyl alcohol at a ratio of 0.9 to 1.2 times the mole of the 3-chloro-4-methylbenzoic acid chloride, the 3-chloro-4-said isopropyl alcohol In methylbenzoic acid chloride, the reaction was conducted dropwise with stirring under conditions of no solvent and a reaction temperature of 60 to 140 ° C.
The reaction product obtained was separated and purified preparation of the formula (1) to give the represented 3-chloro-4-methylbenzoic acid isopropyl in characterized Rukoto 3-chloro-4-methylbenzoic acid isopropyl Is the method.

Claims

3-chloro-4-methylbenzoic acid chloride represented by the following formula (2) is reacted with isopropyl alcohol, when the production of 3-chloro-4-methylbenzoic acid isopropyl represented by the following formula (1),
The isopropyl alcohol is used in a proportion of 0.9 to 1.2 moles of the 3-chloro-4-methylbenzoic acid chloride, and
The isopropyl alcohol is reacted dropwise with stirring in the 3-chloro-4-methylbenzoic acid chloride under conditions of no solvent and a reaction temperature of 60 to 140 ° C. ,
The reaction product obtained was separated and purified production method of the following formula (1) to give the represented 3-chloro-4-methylbenzoic acid isopropyl in characterized Rukoto 3-chloro-4-methylbenzoic acid isopropyl .

Formula 4-methyl-benzoic acid chloride of the formula (3) and Kakushio hydride in the presence of chlorine and Lewis acid catalysts, the 3-chloro-4-methylbenzoic acid chloride represented by the obtained formula (2) In producing isopropyl 3-chloro-4-methylbenzoate represented by the following formula (1) by reacting with isopropyl alcohol ,
In the nuclear chlorination reaction, ferric chloride is used as a Lewis acid catalyst in a proportion of 0.1 to 1.0% by weight, and the reaction is carried out under conditions of no solvent and a chlorine introduction amount of 0.5 times mol or more. And also
The degree of chlorination at the end of the reaction is controlled to be in the range of 0.88 to 0.91, and the reaction vessel is immediately purged with nitrogen after the completion of the reaction.
In the esterification reaction, as well as using the isopropyl alcohol at a ratio of 0.9 to 1.2 times the mole of the 3-chloro-4-methylbenzoic acid chloride, the 3-chloro-4-said isopropyl alcohol In methylbenzoic acid chloride, the reaction was conducted dropwise with stirring under conditions of no solvent and a reaction temperature of 60 to 140 ° C.
The reaction product obtained was separated and purified preparation of represented by 3-chloro-4-methylbenzoic acid to give the isopropyl characterized Rukoto 3-chloro-4-methylbenzoic acid isopropyl by the following formula (1) Method.