JPH0474151A - Production of phenoxycarboxylic acid derivative - Google Patents
Production of phenoxycarboxylic acid derivativeInfo
- Publication number
- JPH0474151A JPH0474151A JP18335690A JP18335690A JPH0474151A JP H0474151 A JPH0474151 A JP H0474151A JP 18335690 A JP18335690 A JP 18335690A JP 18335690 A JP18335690 A JP 18335690A JP H0474151 A JPH0474151 A JP H0474151A
- Authority
- JP
- Japan
- Prior art keywords
- phenoxycarboxylic acid
- acid derivative
- phenoxycarboxylic
- water
- crystals
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000013078 crystal Substances 0.000 claims abstract description 13
- -1 phenoxycarboxylic acid ester Chemical class 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 238000007086 side reaction Methods 0.000 abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 238000000151 deposition Methods 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- MXMQIRYBCYFUOK-UHFFFAOYSA-N 2-(3-methylbut-2-enoxy)-1-phenylethanone Chemical compound CC(C)=CCOCC(=O)C1=CC=CC=C1 MXMQIRYBCYFUOK-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
この発明は、フェノキシカルボン酸誘導体の製造方法に
関するものである。さらに詳しくは、この発明は、医薬
、農薬の合成中間体等として有用なフェノキシカルボン
酸誘導体の高純度、高効率な取得を可能とする改善され
た製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing phenoxycarboxylic acid derivatives. More specifically, the present invention relates to an improved production method that enables highly pure and highly efficient acquisition of phenoxycarboxylic acid derivatives useful as synthetic intermediates for pharmaceuticals and agricultural chemicals.
（従来の技術とその課題）
従来より、各種の置換基や構造を有するフェノキシカル
ボン酸誘導体が数多く知られており、医薬品や農薬、あ
るいはその合成中間体等として利用されてきている。(Prior art and its problems) Many phenoxycarboxylic acid derivatives having various substituents and structures have been known, and have been used as pharmaceuticals, agricultural chemicals, or synthetic intermediates thereof.
これらのフェノキシカルボン酸誘導体の製造においては
、フェノキシ基を有する遊離のカルボン酸を取得するた
めに、たとえば次式
（Ｒ１は置換または非置換フェニル基を示す）で表わさ
れるフェノール誘導体に、
Ｘ−Ｒ，−Ｃｏ−ＯＲ。In the production of these phenoxycarboxylic acid derivatives, in order to obtain a free carboxylic acid having a phenoxy group, for example, a phenol derivative represented by the following formula (R1 represents a substituted or unsubstituted phenyl group) is combined with X-R. ,-Co-OR.
（Ｘはハロゲン原子、Ｒ２はアルキレン基、Ｒ１はアル
キル基を示す）
のカルボン酸エステルを反応させ、次いで、得られた
Ｒｔ ＯＲ２Ｃｏ ＯＲ）
の化合物を加水分解して、次式
Ｒ，０−Ｒ２−Ｃｏ−ＯＨ
のフェノキシカルボン酸誘導体を製造することがしばし
ば行われてきている。(X is a halogen atom, R2 is an alkylene group, and R1 is an alkyl group) is reacted with a carboxylic acid ester of It has often been carried out to prepare phenoxycarboxylic acid derivatives of -Co-OH.
しかしながら、このような遊離のカルボン酸を製造する
従来の方法においては、その加水分解の反応工程に有機
溶媒を使用し、均一系反応として行ってきているため、
高純度品を効率よく取得することが困難であるという問
題があった。However, in conventional methods for producing such free carboxylic acids, organic solvents are used in the hydrolysis reaction step, and the reaction is carried out as a homogeneous system.
There has been a problem in that it is difficult to efficiently obtain high-purity products.
たとえば具体的にも、
のフェノキシカルボン酸エステルを、まずＫＯＨの添加
によってケン化し、次いで中和処理してフェノキシカル
ボン酸に転化する際にエタノール等の有機溶媒中で処理
する方法が知られてもいる（特開昭５２−９７９５０号
公報）。For example, specifically, a method is known in which the phenoxycarboxylic acid ester of is first saponified by adding KOH, and then treated in an organic solvent such as ethanol during neutralization and conversion to phenoxycarboxylic acid. (Japanese Unexamined Patent Publication No. 52-97950).
しかしながら、この方法においても、加水分解により得
られたフェノキシカルボン酸が溶媒に溶解しているため
に、抽出や溶Ｕ留去等の操作が必要となり、その操作は
面倒であり、しかもまた、これらの操作の過程で生成物
の劣化が進行し、不純物の増大や着色が起こり、高純度
、高品質なフェノキシカルボン酸を取得することは困難
であった。また、有機溶媒から一部結晶で得られる場合
にも、その回収効率や純度が高くなかった。However, even in this method, since the phenoxycarboxylic acid obtained by hydrolysis is dissolved in the solvent, operations such as extraction and distillation of dissolved U are required, and these operations are troublesome. During the process, the product deteriorates, impurities increase and coloration occurs, making it difficult to obtain high-purity, high-quality phenoxycarboxylic acid. Furthermore, even when some crystals were obtained from an organic solvent, the recovery efficiency and purity were not high.
この発明は、以上の通りの事情に鑑みてなされたもので
あり、従来のフェノキシカルホン酸エステルの加水分解
によるフェノキシカルボン酸誘導体の製造法の欠点を解
消し、簡便な操作で、しかも高純度、高品質なフェノキ
シカルボン酸誘導体を製造することのできる新しい方法
を提供することを目的としている。This invention was made in view of the above-mentioned circumstances, and it solves the drawbacks of the conventional method for producing phenoxycarboxylic acid derivatives by hydrolyzing phenoxycarboxylic acid esters, and provides a simple operation with high purity. The purpose of the present invention is to provide a new method for producing high-quality phenoxycarboxylic acid derivatives.
（課題を解決するための手段）
この発明は、上記の課題を解決するものとして、Ｒ，０
−Ｒ２−Ｃｏ−０Ｒ。(Means for Solving the Problems) This invention solves the above problems by providing R,0
-R2-Co-0R.
（Ｒ＋は置換または非置換のフェニル基、Ｒ２はアルキ
レン基、Ｒ３はアルキル基を示す）で表わされるフェノ
キシカルボン酸エステル誘導体を水の存在下に加水分解
し、反応系内より次式％式％
のフェノキシカルボン酸誘導体を結晶として取得するこ
とを特徴とするフェノキシカルボン酸誘導体の製造方法
を提供する。(R+ is a substituted or unsubstituted phenyl group, R2 is an alkylene group, and R3 is an alkyl group) is hydrolyzed in the presence of water, and the following formula % formula % Provided is a method for producing a phenoxycarboxylic acid derivative, which comprises obtaining the phenoxycarboxylic acid derivative as a crystal.
この発明の方法は、上記した通り水の存在下で加水分解
することを特徴とするが、この場合、加水分解は実質的
に水のみからなる系において行うものの、有機溶媒が多
少混在していてもよい、具体的には、
Ｒ，０−Ｒ２−Ｃｏ−ＯＲ。As mentioned above, the method of this invention is characterized by hydrolysis in the presence of water. In this case, although the hydrolysis is carried out in a system consisting essentially of water, some organic solvent may be present. Specifically, R,0-R2-Co-OR.
のフェノキシカルボン酸誘導体を水の存在下において、
ＮａＯＨ，ＫＯＨ等のアルカリによってケン化し、次い
で酸水溶液添加等によって中和し、次いで、生成したフ
ェノキシカルボン酸誘導体の結晶を濾過して取得する。of phenoxycarboxylic acid derivative in the presence of water,
It is saponified with an alkali such as NaOH or KOH, then neutralized by addition of an acid aqueous solution, etc., and then the generated crystals of the phenoxycarboxylic acid derivative are obtained by filtration.
ケン化反応は、常法により実施することができ、常温、
もしくは８０℃程度までの温度において実施するのが好
ましい。具体的にはフェノキシカルボン酸誘導体に対し
、当量以上のアルカリを用いて行なう。水の添加量は特
に制限されないが、通常、ケン化反応時に反応系が撹拌
可能になるような量が用いられる。The saponification reaction can be carried out by a conventional method, at room temperature,
Alternatively, it is preferable to carry out at a temperature of up to about 80°C. Specifically, the alkali is used in an amount equivalent or more to the phenoxycarboxylic acid derivative. The amount of water added is not particularly limited, but is usually used in such an amount that the reaction system can be stirred during the saponification reaction.
ケン化反応時のアルカリを水溶液の状態で用いる場合は
新たな水の添加を必要としない場合もある。ケン化反応
の終了後、反応系を室温以下程度に冷却し、中和処理す
るのが好ましい。この中和は、常法により実施すること
ができ、具体的にはケン化反応に用いたアルカリに対し
、当量以上の酸を用いて行なう。酸の種類は特に限定さ
れないが、操作性の面で塩酸、硫酸などの無ｌｌ酸を用
いるのが好ましい。When the alkali used in the saponification reaction is used in the form of an aqueous solution, it may not be necessary to add additional water. After the saponification reaction is completed, the reaction system is preferably cooled to about room temperature or below, and then neutralized. This neutralization can be carried out by a conventional method, and specifically, it is carried out using an acid in an amount equivalent or more to the alkali used in the saponification reaction. The type of acid is not particularly limited, but from the viewpoint of operability, it is preferable to use a free acid such as hydrochloric acid or sulfuric acid.
反応原料となる次式
％式％
のフェノキシカルボン酸エステル誘導体としては、式中
のＲ２としての置換または非置換フェニル基が、アルキ
ル、アルケニル、シクロアルキル、シクロアルケニル、
アリール等の炭化水素基、アルコキシ基、アルケニルオ
キシ基等のエーテル基、ケト基、アルデｂド基、アミノ
基、シアノ基、カルボキシル基、エステル基等の官能基
を１個以上有するか、またはこれらを有しないフェニル
基であるものとすることができる。Ｒ２はメチレン基、
エチレン基、トリメチレン基などのアルキレン基、Ｒ３
はメチル基、エチル基、プロピル基、イソプロピル基、
ペンチル基、ノニル基、デシル基などのアルキル基の適
宜なものとすることかできる。As the phenoxycarboxylic acid ester derivative of the following formula % formula % which is a reaction raw material, the substituted or unsubstituted phenyl group as R2 in the formula is alkyl, alkenyl, cycloalkyl, cycloalkenyl,
Has one or more functional groups such as hydrocarbon groups such as aryl, ether groups such as alkoxy groups and alkenyloxy groups, keto groups, aldebdo groups, amino groups, cyano groups, carboxyl groups, and ester groups, or It can be a phenyl group having no. R2 is a methylene group,
Alkylene groups such as ethylene group and trimethylene group, R3
is a methyl group, an ethyl group, a propyl group, an isopropyl group,
It can be any suitable alkyl group such as a pentyl group, nonyl group, or decyl group.
この発明のフェノキシカルボン酸エステル誘導体は一般
に水不溶性であり、反応に際しては粉体状または微粒状
の形態で系内に供される。しかし、この発明においては
原料のフェノキシカルボン酸エステル誘導体は水に可溶
性または一部が可溶性なものでもよく、必ずしも不溶性
である必要はない。The phenoxycarboxylic acid ester derivative of this invention is generally water-insoluble, and is supplied to the system in the form of powder or fine particles during the reaction. However, in this invention, the raw material phenoxycarboxylic acid ester derivative may be soluble or partially soluble in water, and does not necessarily need to be insoluble.
これらの任意の化合物を原料とし、この発明の水の存在
下での加水分解と結晶としてのフェノキシカルボン酸の
取得とを特徴とする方法によって、簡便な操作で、副反
応を抑制しつつ高純度、高品質なフェノキシカルボン酸
誘導体の取得が可能となる。By using any of these compounds as raw materials and using the method of the present invention, which is characterized by hydrolysis in the presence of water and obtaining phenoxycarboxylic acid as crystals, high purity can be obtained with simple operations while suppressing side reactions. , it becomes possible to obtain high-quality phenoxycarboxylic acid derivatives.
以下、実施例を示し、さらに詳しくこの発明の製造方法
について説明する６
実施例１
２−エトキシカルボニルメチルオキシ−４（３−メチル
−２−ブテニロキシ）アセトフェノン粉体１０． Ｏｆ
を３０．０ｇの水に懸濁させ、６０″Ｃまで昇温させた
後に１０％ＮａＯＨ水溶液１６．４ ｇを滴下し、同温
度で一時間撹拌した。Hereinafter, Examples will be shown and the manufacturing method of the present invention will be explained in more detail.6 Example 1 2-Ethoxycarbonylmethyloxy-4(3-methyl-2-butenyloxy)acetophenone powder 10. Of
was suspended in 30.0 g of water, the temperature was raised to 60''C, 16.4 g of a 10% NaOH aqueous solution was added dropwise, and the mixture was stirred at the same temperature for 1 hour.
攪拌後、均一透明な溶液が得られた。After stirring, a homogeneous clear solution was obtained.
この溶液を室温まで冷却した後に、１０％塩酸水溶液２
５．０ｇを添加した。白色結晶が析出した。After cooling this solution to room temperature, 10% aqueous hydrochloric acid solution 2
5.0g was added. White crystals precipitated.
この結晶を吸引濾過し、得られたケーキを水洗し、６０
℃で減圧乾燥させた。白色結晶の２−カルボキシメチル
オキシ−４−（３−メチル−２−ブテニロキシ）アセト
フェノンからなるフェノキシカルボン酸誘導体９．１ｇ
が得られた。反応収率は９５．９％であった。The crystals were suction filtered, the resulting cake was washed with water,
It was dried under reduced pressure at ℃. 9.1 g of a white crystalline phenoxycarboxylic acid derivative consisting of 2-carboxymethyloxy-4-(3-methyl-2-butenyloxy)acetophenone
was gotten. The reaction yield was 95.9%.
また、使用した原料と、生成物のＨＰＬＣ純度は次の通
りであった。In addition, the raw materials used and the HPLC purity of the product were as follows.
原 料 ９７．６％
生成物 ９９，４％
後述の比較例との対比からも明らかなように、極めて高
純度なフェノキシカルボン酸誘導体か得られる。Raw material: 97.6% Product: 99.4% As is clear from the comparison with the comparative example described later, an extremely highly pure phenoxycarboxylic acid derivative can be obtained.
実施５２
１０％ＮａＯＨ水溶液１６．４ｇを４０℃に加温してお
き、撹拌下に、２−メトキシカルボニルメチルオキシ−
４−（３−メチル−２−ブテニロキシ）アセトフェノン
の粉体１０．Ｏｇを徐々に添加し、加水分解反応を行っ
た。添加終了時にほぼ均一状態となる。反応を完結させ
るなめ、さらに６０°Ｃで１時間撹拌しな。Implementation 52 16.4 g of 10% NaOH aqueous solution was heated to 40°C, and while stirring, 2-methoxycarbonylmethyloxy-
4-(3-methyl-2-butenyloxy)acetophenone powder 10. Og was gradually added to carry out a hydrolysis reaction. At the end of the addition, the mixture becomes almost uniform. Stir for an additional 1 hour at 60°C to complete the reaction.
室温まで冷却した後に、１０％塩酸水溶液１５．８ｇを
添加し、酸性化した。白色結晶が析出した。After cooling to room temperature, 15.8 g of a 10% aqueous hydrochloric acid solution was added for acidification. White crystals precipitated.
さらに０℃まで冷却し、次いで吸引沢過し、得られたケ
ーキを水洗し、６０℃で減圧乾燥させた。The mixture was further cooled to 0°C, filtered under suction, and the resulting cake was washed with water and dried under reduced pressure at 60°C.
白色結晶の２−カルボキシメチルオキシ−４（３−メチ
ル−２−ブテニロキシ）アセトフェノンからなるフェノ
キシカルボン酸誘導体を９，３ｇ得た。反応収率は、９
９．７％であった。9.3 g of a phenoxycarboxylic acid derivative consisting of 2-carboxymethyloxy-4(3-methyl-2-butenyloxy)acetophenone in the form of white crystals was obtained. The reaction yield is 9
It was 9.7%.
原料および生成物のＨＰＬＣ純度は、次の通りであった
６
原 料 ９７．８％
生成物 ９９．８％
比較例１
２−エトキシカルボニルメチルオキシ−４（３−メチル
−２−ブテニロキシ）アセトフェノン２．５ｇに、１ｇ
のＫＯＨを溶解した３０ｍ１エタノールを加えて還流し
た。１時間の還流の後に希塩酸水溶液を加えて中和し、
エーテルにより抽出（３回）した。The HPLC purity of the raw material and product was as follows6 Raw material 97.8% Product 99.8% Comparative Example 1 2-Ethoxycarbonylmethyloxy-4(3-methyl-2-butenyloxy)acetophenone 2 .5g to 1g
30ml of ethanol in which KOH was dissolved was added and refluxed. After refluxing for 1 hour, neutralize by adding dilute aqueous hydrochloric acid solution,
Extracted with ether (3 times).
エーテル抽出層を洗浄および乾燥し、エーテルを留去し
たところ、淡黄色結晶の２−カルボキシメチルオキシ−
４−（３−メチル−２−ブテニロキシ）アセトフェノン
からなるフェノキシカルボン酸誘導体２．０ｇを得た。The ether extract layer was washed and dried, and the ether was distilled off, resulting in pale yellow crystals of 2-carboxymethyloxy-
2.0 g of a phenoxycarboxylic acid derivative consisting of 4-(3-methyl-2-butenyloxy)acetophenone was obtained.
反応収率は８８．５％であった。The reaction yield was 88.5%.
また、原料および生成物のＨＰＬＣ純度は次の通りであ
った。In addition, the HPLC purity of the raw materials and products were as follows.
原料 ９７，６％
生成！！’ｋ ９２．４％
（発明の効果）
以上詳しく説明した通り、この発明の製造方法により、
１）従来の有機溶媒を使用する方法に欠かせない抽出、
溶媒留去、再結晶等の面倒な操作を全く必要としない。Raw materials 97.6% produced! ! 'k 92.4% (Effects of the Invention) As explained in detail above, the production method of the present invention achieves 1) extraction, which is indispensable to conventional methods using organic solvents;
Troublesome operations such as solvent distillation and recrystallization are not required at all.
生成物フェノキシカルボン酸誘導体は、反応系より結晶
として析出し、従来のような操作は不要となる。The product phenoxycarboxylic acid derivative is precipitated as crystals from the reaction system, making conventional operations unnecessary.
２） しかも、ケン化、中和、晶析、濾過の操作が連続
的に短時間で実施できるなめ、副反応が起こりに＜＜、
着色もなく、高純度、高品質なフェノキシカルボン酸誘
導体の取得が可能となる。2) Moreover, since the operations of saponification, neutralization, crystallization, and filtration can be performed continuously in a short time, side reactions are less likely to occur.
It becomes possible to obtain a highly pure and high quality phenoxycarboxylic acid derivative without coloring.
Claims (1)
ルキレン基、Ｒ＿３はアルキル基を示す）で表わされる
フェノキシカルボン酸エステル誘導体を水の存在下に加
水分解し、反応系内より次式Ｒ＿１Ｏ−Ｒ＿２−ＣＯ−
ＯＨ のフェノキシカルボン酸誘導体を結晶として取得するこ
とを特徴とするフェノキシカルボン酸誘導体の製造方法
。(1) A phenoxycarboxylic acid ester derivative represented by the following formula R_1O-R_2-CO-OR_3 (R_1 is a substituted or unsubstituted phenyl group, R_2 is an alkylene group, and R_3 is an alkyl group) is hydrated in the presence of water. Decomposed, the following formula R_1O-R_2-CO- is produced from inside the reaction system.
1. A method for producing a phenoxycarboxylic acid derivative, which comprises obtaining a phenoxycarboxylic acid derivative of OH 2 as a crystal.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18335690A JPH0474151A (en) | 1990-07-11 | 1990-07-11 | Production of phenoxycarboxylic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18335690A JPH0474151A (en) | 1990-07-11 | 1990-07-11 | Production of phenoxycarboxylic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0474151A true JPH0474151A (en) | 1992-03-09 |
Family
ID=16134318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18335690A Pending JPH0474151A (en) | 1990-07-11 | 1990-07-11 | Production of phenoxycarboxylic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0474151A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52939A (en) * | 1975-06-17 | 1977-01-06 | Rohm & Haas | Thermosetting coat composite |
-
1990
- 1990-07-11 JP JP18335690A patent/JPH0474151A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52939A (en) * | 1975-06-17 | 1977-01-06 | Rohm & Haas | Thermosetting coat composite |
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