JP6652205B1 - Method for producing ester compound - Google Patents

Method for producing ester compound Download PDF

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JP6652205B1
JP6652205B1 JP2019016771A JP2019016771A JP6652205B1 JP 6652205 B1 JP6652205 B1 JP 6652205B1 JP 2019016771 A JP2019016771 A JP 2019016771A JP 2019016771 A JP2019016771 A JP 2019016771A JP 6652205 B1 JP6652205 B1 JP 6652205B1
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methoxymethyl
propenyl
dimethyl
methyl
tetrafluorophenyl
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JP2020125244A (en
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健二 新井
健二 新井
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Sumitomo Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
    • C07C69/747—Chrysanthemumic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods

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Abstract

【課題】[4-(メトキシメチル)-2,3,5,6-テトラフルオロフェニル]メチル 2,2-ジメチル-3-((Z)-1-プロペニル)シクロプロパンカルボキシラート製造時の不純物生成を抑制する。【解決手段】有機溶媒中で2,2-ジメチル-3-((Z)-1-プロペニル)シクロプロパンカルボン酸メチルと[4-(メトキシメチル)-2,3,5,6-テトラフルオロフェニル]メタノールとをリチウムメトキシドの存在下に反応させて[4-(メトキシメチル)-2,3,5,6-テトラフルオロフェニル]メチル 2,2-ジメチル-3-((Z)-1-プロペニル)シクロプロパンカルボキシラートを製造する上で、有機溶媒、2,2-ジメチル-3-((Z)-1-プロペニル)シクロプロパンカルボン酸メチル及び[4-(メトキシメチル)-2,3,5,6-テトラフルオロフェニル]メタノールの混合物を亜硫酸水素塩水溶液で洗浄した後、リチウムメトキシドを加えて反応を行うことにより、不純物の生成を抑制して目的物を製造することができる。【選択図】なしPROBLEM TO BE SOLVED: To produce impurities in the production of [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate. Suppress. SOLUTION: Methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate and [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl in an organic solvent ] With methanol in the presence of lithium methoxide to give [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1- In producing (propenyl) cyclopropanecarboxylate, an organic solvent, methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate and [4- (methoxymethyl) -2,3, After washing a mixture of 5,6-tetrafluorophenyl] methanol with an aqueous solution of bisulfite, lithium methoxide is added to carry out the reaction, whereby the production of the desired product can be suppressed while suppressing the generation of impurities. [Selection diagram] None

Description

本発明はエステル化合物の製造方法に関する。   The present invention relates to a method for producing an ester compound.

［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートが殺虫活性を有することが知られている。（特許文献１）
［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートは、２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボン酸メチル、ヘプタン及び［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メタノールの混合物にリチウムメトキシドを加えて反応させることにより製造することができる。（特許文献２） It is known that [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate has insecticidal activity. Have been. (Patent Document 1)
[4- (Methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate is 2,2-dimethyl- Lithium methoxide is added to a mixture of methyl 3-((Z) -1-propenyl) cyclopropanecarboxylate, heptane and [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methanol and reacted. It can be manufactured by doing. (Patent Document 2)

ＵＳ６２２５４９５US6225495 特開２００５−８２５０１JP-A-2005-85001

特許文献２には［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートを工業的に製造する上で有利な方法が開示されている。   Patent Document 2 discloses that [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate is industrially used. Discloses an advantageous method for manufacturing.

この方法によれば、水蒸気蒸留の後、精留塔の底部より目的物が得られるが、その際に例えば、下記の式（Ａ）で示される化合物のような分子量の大きい不純物が残ることがある。   According to this method, after steam distillation, the target product is obtained from the bottom of the rectification column. At this time, impurities having a high molecular weight such as a compound represented by the following formula (A) may remain. is there.

本発明は、式（Ａ）

Figure 0006652205
The present invention provides a compound of the formula (A)
Figure 0006652205

で示される化合物（以下、化合物（Ａ）と記す）が不純物として生成することを抑制して［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートを製造する方法を提供することを課題とする。 [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl An object of the present invention is to provide a method for producing -3-((Z) -1-propenyl) cyclopropanecarboxylate.

本発明は、２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボン酸メチル、有機溶媒及び［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メタノールの混合物にリチウムメトキシドを加えて反応させて［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートを製造する際に、予め該混合物を亜硫酸水素塩水溶液で洗浄することにより、化合物（Ａ）が不純物として生成することを抑制できるというものである。   The present invention relates to methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate, an organic solvent and [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl]. Lithium methoxide was added to a mixture of methanol and reacted to give [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl). ) When producing the cyclopropane carboxylate, by washing the mixture in advance with an aqueous bisulfite solution, it is possible to suppress the formation of the compound (A) as an impurity.

本発明により、不純物の生成を抑制して［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートを製造することができる。   According to the present invention, generation of impurities is suppressed and [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclo Propane carboxylate can be produced.

本発明の製造方法は、特開２００５−８２５０１を参考にして行うことができる。   The production method of the present invention can be performed with reference to JP-A-2005-82501.

即ち、２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボン酸メチル、有機溶媒及び［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メタノールの混合物にリチウムメトキシドを加えて反応を行うが、予め、該混合物を亜硫酸水素塩水溶液で洗浄することが必要である。   That is, methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate, an organic solvent and [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methanol The reaction is carried out by adding lithium methoxide to the mixture. It is necessary to wash the mixture with an aqueous bisulfite solution in advance.

亜硫酸水素塩は水溶性の塩であれば特に制限されないが、通常はアルカリ金属塩、特に入手性の良いナトリウム塩が通常使用される。特に、亜硫酸水素ナトリウムの１〜１０重量％水溶液を使用するのが好ましい。   The bisulfite is not particularly limited as long as it is a water-soluble salt, but usually an alkali metal salt, particularly a readily available sodium salt, is usually used. In particular, it is preferable to use a 1 to 10% by weight aqueous solution of sodium bisulfite.

亜硫酸水素塩水溶液で洗浄する際、該水溶液に亜硫酸ナトリウム等の亜硫酸塩を加えてもよい。   When washing with a bisulfite aqueous solution, a sulfite such as sodium sulfite may be added to the aqueous solution.

２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボン酸メチルは［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メタノール１モルに対して通常１〜３モルの割合で使用され、有機溶媒は［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メタノール１重量部に対して通常１〜１０重量部使用される。   Methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate is usually added to 1 mol of [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methanol. The organic solvent is used in an amount of 1 to 3 mol, and usually 1 to 10 parts by weight based on 1 part by weight of [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methanol.

有機溶媒としては、例えば脂肪族炭化水素、芳香族炭化水素、ハロゲン化炭化水素が挙げられ、ヘプタンが好ましい。   Examples of the organic solvent include aliphatic hydrocarbons, aromatic hydrocarbons, and halogenated hydrocarbons, and heptane is preferred.

亜硫酸水素塩水溶液で洗浄した混合物にリチウムメトキシドを加えて反応を行うが、リチウムメトキシドを加える際の温度は５０〜２００℃が好ましく、さらにその後８０〜１５０℃にて１０〜４８時間保温するのが好ましい。   Lithium methoxide is added to the mixture washed with the bisulfite aqueous solution to carry out the reaction. The temperature at the time of adding lithium methoxide is preferably 50 to 200 ° C., and further kept at 80 to 150 ° C. for 10 to 48 hours. Is preferred.

反応終了後は反応混合物を水又はアルカリ水で洗浄し、さらに必要のより酸性水で洗浄して油相を取り出し、精留塔を備えた蒸留装置で水蒸気蒸留を行うことにより、精留塔の底部に残る油相として［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートを得ることができる。   After the completion of the reaction, the reaction mixture is washed with water or alkaline water, and further washed with acidic water as needed to take out an oil phase, and steam distillation is performed by a distillation apparatus equipped with a rectification column, whereby the rectification column is removed. [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate is obtained as the oil phase remaining at the bottom be able to.

２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボン酸メチル ９．３８ｇ、［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メタノール １０．２ｇ、２,６−ジ−ｔｅｒｔ−ブチル−ｐ−クレゾール ０．１５ｇ、ヘプタン １０．２ｇ、１重量％の亜硫酸水素ナトリウム水溶液 １０．０ｇを混合し、４０〜５０℃で３０分間洗浄した後、分液し水層を取り除いた。更に水 ５．０ｇで同様に洗浄した後に、ヘプタン ３０．６ｇ、リチウムメトキシド ０．０５９ｇを加え、［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メタノールが［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートに対して２％以下になるまで１０２℃にて生成するメタノールを除きながら加熱還流した。その後、室温まで冷却し水で洗浄後、ヘプタン溶液を減圧濃縮し、４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラート１７．３ｇを油状物として得た。得られた２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートの液体クロマトグラフィー分析によって化合物（Ａ）の含有量を測定した。同様に、亜硫酸水素ナトリウム溶液の濃度を変更し、化合物（Ａ）の含有量を測定した。亜硫酸水素ナトリウム水溶液で洗浄しない場合は、続く水による洗浄も省略した。

Figure 0006652205
9.38 g of methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate, 10.2 g of [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methanol After mixing 0.15 g of 2,6-di-tert-butyl-p-cresol, 10.2 g of heptane and 10.0 g of a 1% by weight aqueous solution of sodium bisulfite, the mixture was washed at 40 to 50 ° C. for 30 minutes, and then mixed. The liquor aqueous layer was removed. After further washing with 5.0 g of water in the same manner, 30.6 g of heptane and 0.059 g of lithium methoxide were added, and [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methanol was added to [4 -(Methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropane The mixture was heated to reflux while removing methanol produced at ℃. Then, after cooling to room temperature and washing with water, the heptane solution was concentrated under reduced pressure, and 4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) 17.3 g of (-1-propenyl) cyclopropanecarboxylate were obtained as an oil. The content of the compound (A) was measured by liquid chromatography analysis of the obtained 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate. Similarly, the concentration of the sodium bisulfite solution was changed, and the content of the compound (A) was measured. When washing with an aqueous solution of sodium bisulfite was not performed, washing with subsequent water was also omitted.

Figure 0006652205

（＊） １％ＮａＨＳＯ３の他に０．５％Ｎａ２ＳＯ３を含む水溶液を使用

上表に見られるように、亜硫酸水素塩水溶液で洗浄することにより、不純物である化合物（Ａ）の生成を抑制することができる。 (*) Use aqueous solution containing 0.5% Na 2 SO 3 in addition to 1% NaHSO 3

As can be seen from the above table, the generation of the compound (A) as an impurity can be suppressed by washing with the bisulfite aqueous solution.

本発明の製造方法により、殺虫活性を有する［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートを製造することができる。   According to the production method of the present invention, [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclo having insecticidal activity. Propane carboxylate can be produced.

Claims (4)

有機溶媒中で２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボン酸メチルと［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メタノールとをリチウムメトキシドの存在下に反応させて［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートを製造する方法において、有機溶媒、２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボン酸メチル及び［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メタノールの混合物を亜硫酸水素塩水溶液で洗浄した後、該混合物にリチウムメトキシドを加えて反応を行う［４−（メトキシメチル）−２，３，５，６−テトラフルオロフェニル］メチル ２，２−ジメチル−３−（（Ｚ）−１−プロペニル）シクロプロパンカルボキシラートの製造方法。   Methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate and [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methanol in an organic solvent Reaction in the presence of lithium methoxide to give [4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropane In a method for producing a carboxylate, an organic solvent, methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate and [4- (methoxymethyl) -2,3,5,6- After washing a mixture of [tetrafluorophenyl] methanol with an aqueous bisulfite solution, lithium methoxide is added to the mixture to carry out a reaction [4- (methoxymethyl). 2,3,5,6-tetrafluoro phenyl] methyl 2,2-dimethyl -3 - ((Z) -1- propenyl) method for producing cyclopropanecarboxylate. 亜硫酸水素塩が亜硫酸水素ナトリウムである請求項１に記載の方法。   The method of claim 1 wherein the bisulfite is sodium bisulfite. 亜硫酸水素塩水溶液が、濃度が１〜１０重量％の亜硫酸水素ナトリウム水溶液である請求項１に記載の方法。   The method according to claim 1, wherein the bisulfite aqueous solution is a sodium bisulfite aqueous solution having a concentration of 1 to 10% by weight. 有機溶媒がヘプタンである請求項１〜３のいずれかに記載の方法。   The method according to any one of claims 1 to 3, wherein the organic solvent is heptane.
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