JPH02138148A - Production of optically active 2-phenoxybutanoic acid - Google Patents
Production of optically active 2-phenoxybutanoic acidInfo
- Publication number
- JPH02138148A JPH02138148A JP29244288A JP29244288A JPH02138148A JP H02138148 A JPH02138148 A JP H02138148A JP 29244288 A JP29244288 A JP 29244288A JP 29244288 A JP29244288 A JP 29244288A JP H02138148 A JPH02138148 A JP H02138148A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- formula
- alkali metal
- optically active
- acid
- 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.)
- Granted
Links
- TVSPPYGAFOVROT-UHFFFAOYSA-N 2-phenoxybutanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC=C1 TVSPPYGAFOVROT-UHFFFAOYSA-N 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
- -1 alkali metal salt Chemical class 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 19
- 230000003287 optical effect Effects 0.000 abstract description 16
- 239000002904 solvent Substances 0.000 abstract description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000010 aprotic solvent Substances 0.000 abstract description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000007858 starting material Substances 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 239000002798 polar solvent Substances 0.000 abstract description 2
- 239000007810 chemical reaction solvent Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RVBUZBPJAGZHSQ-GSVOUGTGSA-N (2r)-2-chlorobutanoic acid Chemical compound CC[C@@H](Cl)C(O)=O RVBUZBPJAGZHSQ-GSVOUGTGSA-N 0.000 description 2
- RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical compound CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 description 2
- DHPCRFYUUWAGAH-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)phenol Chemical compound OC1=CC=C(F)C(C(F)(F)F)=C1 DHPCRFYUUWAGAH-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YAQLSKVCTLCIIE-GSVOUGTGSA-N (2r)-2-bromobutanoic acid Chemical compound CC[C@@H](Br)C(O)=O YAQLSKVCTLCIIE-GSVOUGTGSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- VYCUUOHOBUPEPJ-UHFFFAOYSA-N 2-phenoxybutanamide Chemical class CCC(C(N)=O)OC1=CC=CC=C1 VYCUUOHOBUPEPJ-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003579 shift reagent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、農薬の合成中間体として有用な光学活性な２
−フェノキシブタン酸の製造方法に関する。Detailed Description of the Invention (Field of Industrial Application) The present invention provides an optically active compound useful as a synthetic intermediate for agricultural chemicals.
-Regarding a method for producing phenoxybutanoic acid.
フェノキシブタン酸誘導体には生物活性を示す化合物が
多く知られている０例えば特開昭５８−１１３１５５号
、特開昭５８−６７６５３号、特開昭５９−２９６４５
号公報に示されている２−フェノキシブタン酸アミド類
は、農薬とくに除草剤として有用である。Many phenoxybutanoic acid derivatives are known to exhibit biological activity.
The 2-phenoxybutanoic acid amides disclosed in the publication are useful as agricultural chemicals, especially herbicides.
（従来の技術及び発明が解決しようとする課ＩＩ）２−
フェノキシブタン酸は２位に不斉炭素原子を有し、光学
活性な２−フェノキシブタン酸を製造する方法は、従来
全く知られていない、そこで光学活性なアミン類と（±
）−２−フェノキシブタン酸とのジアステレオマー塩に
よる光学分割法を試みた。(Question II to be solved by the prior art and the invention) 2-
Phenoxybutanoic acid has an asymmetric carbon atom at the 2-position, and there is no known method for producing optically active 2-phenoxybutanoic acid.
)-2-Phenoxybutanoic acid and an optical resolution method using diastereomeric salts were attempted.
しかしながら、この方法で光学純度の高い２−フェノキ
シブタン酸を得るには、数回以上の再結晶を必要とし、
さらにごく限られた条件でしか分割できないなど、操作
上大きな問題があった。さらに用いたラセミ体に対する
光学活性体の回収率も不充分であった。However, in order to obtain 2-phenoxybutanoic acid with high optical purity using this method, recrystallization is required several times or more.
Furthermore, there were major operational problems, such as the fact that it could only be divided under very limited conditions. Furthermore, the recovery rate of the optically active form relative to the racemic form used was also insufficient.
従って、このような分割法は少量の場合には適用可能で
あるが、工業的に大量を製造するのにこの方法を適用す
ることは非常に困難であった。Therefore, although such a division method is applicable to small quantities, it has been very difficult to apply this method to industrial production of large quantities.
（課題を解決するための手段）
本発明者等は、工業的に光学活性な２−フェノキシブタ
ン酸の製造法を鋭意研究し、本発明をなすに至った。(Means for Solving the Problems) The present inventors have conducted intensive research on a method for industrially producing optically active 2-phenoxybutanoic acid, and have accomplished the present invention.
本発明は
入
（式中、Ｘは塩素原子又は臭素原子を表し、Ｍはアルカ
リ金属原子を表す）で示される光学活性な２−ハロゲノ
ブタン酸のアルカリ金属塩と（式中、Ｙはハロゲン原子
、低級アルキル基又はトリフルオロメチル基を表し、ｎ
は１〜３の整数を表し、Ｍはアルカリ金属原子を表す）
で示されるフェノールのアルカリ金属塩とを反応させる
ことを特徴とする。The present invention relates to an optically active alkali metal salt of 2-halogenobutanoic acid represented by (wherein, X represents a chlorine atom or a bromine atom, and M represents an alkali metal atom); Represents a lower alkyl group or trifluoromethyl group, n
represents an integer from 1 to 3, M represents an alkali metal atom)
It is characterized by reacting with an alkali metal salt of phenol shown in
式
（式中、Ｙ及びｎは前記と同義である）で示される活性
な２−フェノキシブタン酸の製造法である。This is a method for producing active 2-phenoxybutanoic acid represented by the formula (wherein Y and n have the same meanings as above).
上記式（Ｉ）及び式（ＩＩ）の原料化合物は、各々あら
かじめ別途合成して用いるか、溶媒中で合成してそのま
ま用いてもよい０反応は以下のような溶媒中で行われる
。The starting compounds of formula (I) and formula (II) may be synthesized separately in advance and used, or may be synthesized in a solvent and used as they are.The reaction is carried out in the following solvent.
この反応に用いる溶媒としては、Ｎ、Ｎ−ジメチルホル
ムアミド（ＤＭＦ）、ジメチルスルホキサイド（ＤＭＳ
Ｏ）、１．３−ジメチル−２−イミダゾリジノン（ＤＭ
Ｉ）、ヘキサメチルホスホリックアミドなどの双極性非
プロトン溶媒又は水、アルコール等の極性溶媒を単独で
用いるかあるいは双極性非プロトン溶媒の場合はベンゼ
ン、トルエン、キシレン等の非プロトン溶媒との混合温
媒として用いることができる。Solvents used in this reaction include N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMS
O), 1,3-dimethyl-2-imidazolidinone (DM
I) dipolar aprotic solvents such as hexamethylphosphoric amide or polar solvents such as water or alcohol are used alone or in the case of dipolar aprotic solvents, they are mixed with aprotic solvents such as benzene, toluene, xylene, etc. It can be used as a heating medium.
溶媒量としては、基質１重量部に対し、単独溶媒の場合
は１〜１０重量部の溶媒を用い、混合溶媒の場合は、双
極性非プロトン溶媒を０．３〜５重量部と非プロトン性
溶媒１〜１０重量部を混合して用いると良好に反応が進
行し好ましい。As for the amount of solvent, for 1 part by weight of the substrate, use 1 to 10 parts by weight of the solvent in the case of a single solvent, and in the case of a mixed solvent, use 0.3 to 5 parts by weight of the dipolar aprotic solvent. It is preferable to use a mixture of 1 to 10 parts by weight of the solvent because the reaction proceeds well.
反応温度は０−１００℃で、特に２０〜５０℃が好まし
い０反応時間は特に限定されないが、溶媒等により異な
り、５〜２０時間でほぼ完結する。The reaction temperature is 0 to 100°C, preferably 20 to 50°C. The reaction time is not particularly limited, but varies depending on the solvent and the like, and the reaction is almost completed in 5 to 20 hours.
出発原料は、光学活性の２−ハロゲノブタン酸のアルカ
リ金属塩（Ｉ）１当量に対し、フェノールのアルカリ金
属塩（ＩＩ）０．８〜５当量を用いるとよい。As the starting material, it is preferable to use 0.8 to 5 equivalents of the alkali metal salt of phenol (II) per 1 equivalent of the optically active alkali metal salt of 2-halogenobutanoic acid (I).
以下に実施例を示し、さらに説明する。Examples will be shown and further explained below.
また、ここで用いた光学活性の２−ハロゲノブタン酸の
光学純度は光学活性を維持したままでメチルエステルに
導き、シフト試薬（ユーロピウム（ＨＦＣ）３）を用い
、ＮＭＲより求めた。さらに得られた２−フェノキシブ
タン酸の光学純度は、あらかじめ光学分割により得られ
た光学純度が１００％の標準品の旋光度を基に算出した
。Further, the optical purity of the optically active 2-halogenobutanoic acid used here was determined by converting it into a methyl ester while maintaining its optical activity and using a shift reagent (europium (HFC) 3) by NMR. Further, the optical purity of the obtained 2-phenoxybutanoic acid was calculated based on the optical rotation of a standard product with an optical purity of 100% obtained in advance by optical resolution.
実施例Ｉ ＤＭＦ中でのＳ−（−） −２−（４−フ
ルオロ−３−トリフルオロメチル）フェノキシブタン酸
の製造
Ｒ−（＋）−２−クロロブタン酸のカリウム塩１６．０
５ｇ （０，１ｍｏｆ）と、４−フルオロ−３−トリフ
ルオロメチルフェノールのカリウム塩３２．７ｇ （０
，１５ｎ＋ｏｆ）を、６０−のＤＭＦ中に加え、２７〜
３０℃で１０時間攪拌した。攪拌終了後、２Ｎ塩酸水溶
液でｐｕｔとして遊離した油状物をエーテルで抽出後、
エーテル層を飽和重曹水溶液で洗浄した。この飽和重曹
水溶液を２Ｎ−塩酸で９１（１とし、再び遊離した油状
物をエーテル抽出した。エーテルを無水硫酸マグネシウ
ムで乾燥後、減圧留去し、残渣を減圧蒸留して目的物を
得た。Example I Preparation of S-(-)-2-(4-fluoro-3-trifluoromethyl)phenoxybutanoic acid in DMF Potassium salt of R-(+)-2-chlorobutanoic acid 16.0
5 g (0.1 mof) and 32.7 g (0.1 mof) of the potassium salt of 4-fluoro-3-trifluoromethylphenol.
, 15n+of) in 60- DMF, 27-
The mixture was stirred at 30°C for 10 hours. After stirring, put in a 2N aqueous hydrochloric acid solution and extract the liberated oil with ether.
The ether layer was washed with a saturated aqueous sodium bicarbonate solution. This saturated aqueous sodium bicarbonate solution was made up to 91 (1) with 2N-hydrochloric acid, and the liberated oil was extracted with ether. The ether was dried over anhydrous magnesium sulfate, then distilled off under reduced pressure, and the residue was distilled under reduced pressure to obtain the desired product.
ｂ、ｐ、１５５〜１６０℃／ ４ ｍｍＨｇ 収率８
１％用いた光学活性な２−クロロブタン酸の光学純度は
ｅｅ＝ ９２％、得られたフェノキシブタン酸の光学純
度はｅｅ＝ ９０％であった。b, p, 155-160℃/4 mmHg Yield 8
The optical purity of optically active 2-chlorobutanoic acid used at 1% was ee = 92%, and the optical purity of the obtained phenoxybutanoic acid was ee = 90%.
実施例２ ＤＭＩ−ベンゼン系でのＳ−（−）−２−
（４−フルオロ−３−トリフルオロメチル）フェノキシ
ブタン酸の合成
Ｒ−（＋） −２−クロロブタン酸のカリウム塩１６．
０５ｇ （０，１ｍｏｊ）と、４−フルオロ−３−トリ
フルオロメチルフェノールのカリウム塩２１、８ｇ （
０，１ｍｏ７）を、ベンゼン７０−とＤＭ１１２Ｒ１１
の混合溶媒中に加え、３０℃で８時間撹拌した。撹拌終
了後、２Ｎ塩酸水溶液でｐＨ１とし、さらにベンゼン２
００Ｒ１を加＾、ベンゼン層を分離後、水洗、ベンゼン
を減圧留去し、残渣を減圧蒸留して目的物２２ｇを得た
。収率８０％。Example 2 S-(-)-2- in DMI-benzene system
Synthesis of (4-fluoro-3-trifluoromethyl)phenoxybutanoic acid Potassium salt of R-(+)-2-chlorobutanoic acid 16.
05 g (0,1 moj) and 21,8 g potassium salt of 4-fluoro-3-trifluoromethylphenol (
0.1mo7), benzene70- and DM112R11
and stirred at 30° C. for 8 hours. After stirring, the pH was adjusted to 1 with 2N aqueous hydrochloric acid solution, and then benzene 2
After adding 00R1^ and separating the benzene layer, the benzene layer was washed with water, the benzene was distilled off under reduced pressure, and the residue was distilled under reduced pressure to obtain 22 g of the target product. Yield 80%.
用いた光学活性な２−クロロブタン酸の光学純度はｅｅ
＝ ９８％、得られたフェノキシブタン酸の光学純度は
ｅｅ＝ ９６％であった。The optical purity of the optically active 2-chlorobutanoic acid used is ee
= 98%, and the optical purity of the obtained phenoxybutanoic acid was ee = 96%.
実施例３ 水溶媒でのＲ−（＋）−２−（４−フルオロ
−３−トリフルオロメチル）フェノキシブタン酸の合成
水１４１ＪにＫＯＨ１４ｇを加え、さらに、４−フルオ
ロ−３−トリフルオロメチル−フェノール２７ ｇ （
０，１５ｍｏ７）と、Ｓ−（−）−２−ブロモブタン酸
１６． ７ｇ （０，１ｍｏ７１とを順次加え、３０℃
で８時間撹拌した。撹拌終了後、２Ｎ塩酸水溶液でｐＨ
１とし、以下実施例１と同様の操作により、目的物２０
．７ｇを得た。収率７８％。Example 3 Synthesis of R-(+)-2-(4-fluoro-3-trifluoromethyl)phenoxybutanoic acid in water solvent 14 g of KOH was added to 141 J of water, and further 4-fluoro-3-trifluoromethyl- 27 g of phenol (
0,15mo7) and S-(-)-2-bromobutanoic acid 16. Add 7g (0, 1mo71) sequentially and heat at 30°C.
The mixture was stirred for 8 hours. After stirring, adjust the pH with 2N hydrochloric acid aqueous solution.
1, and by the same operation as in Example 1, the target object 20
．． 7g was obtained. Yield 78%.
用いたＲ−（＋）−２−ブロモブタン酸の光学純度はｅ
ｅ＝ ９６％、得られたフェノキシブタン酸の光学純度
はｅｅ＝ ９２％であった。The optical purity of the R-(+)-2-bromobutanoic acid used was e
e = 96%, and the optical purity of the obtained phenoxybutanoic acid was ee = 92%.
以上の実施例および種々の条件での実施例を表−１にま
とめて示す。The above examples and examples under various conditions are summarized in Table 1.
（発明の効果）
上記実施例から明らかなように、本発明の方法によれば
高収率で、また高い光学純度で目的とする光学活性のフ
ェノキシブタン酸を得ることができる。(Effects of the Invention) As is clear from the above examples, according to the method of the present invention, the desired optically active phenoxybutanoic acid can be obtained in high yield and with high optical purity.
手続補正書 平成 １月２６日Procedural amendment Heisei January 26th
Claims (1)
リ金属原子を表す）で示される光学活性な２−ハロゲノ
ブタン酸のアルカリ金属塩と 式▲数式、化学式、表等があります▼ （式中、Ｙはハロゲン原子、低級アルキル基又はトリフ
ルオロメチル基を表し、ｎは１〜３の整数を表し、Ｍは
アルカリ金属原子を表す）で示されるフェノールのアル
カリ金属塩とを反応させることを特徴とする。 式 ▲数式、化学式、表等があります▼ （式中、Ｙ及びｎは前記と同義である） で示される光学活性な２−フェノキシブタン酸の製造法
。[Claims] Optically active 2-halogenobutanoic acid represented by the formula ▲ Numerical formula, chemical formula, table, etc. ▼ (wherein, X represents a chlorine atom or a bromine atom, and M represents an alkali metal atom). Alkali metal salts and formulas ▲ There are mathematical formulas, chemical formulas, tables, etc. It is characterized by reacting with an alkali metal salt of phenol represented by A method for producing optically active 2-phenoxybutanoic acid represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, Y and n have the same meanings as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63292442A JPH0791217B2 (en) | 1988-11-21 | 1988-11-21 | Process for producing optically active 2-phenoxybutanoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63292442A JPH0791217B2 (en) | 1988-11-21 | 1988-11-21 | Process for producing optically active 2-phenoxybutanoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02138148A true JPH02138148A (en) | 1990-05-28 |
| JPH0791217B2 JPH0791217B2 (en) | 1995-10-04 |
Family
ID=17781848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63292442A Expired - Lifetime JPH0791217B2 (en) | 1988-11-21 | 1988-11-21 | Process for producing optically active 2-phenoxybutanoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0791217B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016508523A (en) * | 2013-02-28 | 2016-03-22 | プロノヴァ・バイオファーマ・ノルゲ・アーエスＰｒｏｎｏｖａ ＢｉｏＰｈａｒｍａ Ｎｏｒｇｅ ＡＳ | Method for preparing 2-((5Z, 8Z, 11Z, 14Z, 17Z) -icosa-5,8,11,14,17-pentaenyloxy) butanoic acid |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50140632A (en) * | 1974-04-10 | 1975-11-11 | ||
| JPS5217431A (en) * | 1975-06-26 | 1977-02-09 | Stauffer Chemical Co | Phenoxyalkylamides and tickcide containing the same |
| JPS5562043A (en) * | 1978-11-01 | 1980-05-10 | Ihara Chem Ind Co Ltd | Preparation of phenoxycarboxylic acid derivative |
-
1988
- 1988-11-21 JP JP63292442A patent/JPH0791217B2/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50140632A (en) * | 1974-04-10 | 1975-11-11 | ||
| JPS5217431A (en) * | 1975-06-26 | 1977-02-09 | Stauffer Chemical Co | Phenoxyalkylamides and tickcide containing the same |
| JPS5562043A (en) * | 1978-11-01 | 1980-05-10 | Ihara Chem Ind Co Ltd | Preparation of phenoxycarboxylic acid derivative |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016508523A (en) * | 2013-02-28 | 2016-03-22 | プロノヴァ・バイオファーマ・ノルゲ・アーエスＰｒｏｎｏｖａ ＢｉｏＰｈａｒｍａ Ｎｏｒｇｅ ＡＳ | Method for preparing 2-((5Z, 8Z, 11Z, 14Z, 17Z) -icosa-5,8,11,14,17-pentaenyloxy) butanoic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0791217B2 (en) | 1995-10-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO177637B (en) | Process for the preparation of a biphenyl derivative | |
| US4144397A (en) | Preparation of 2-aryl-propionic acids by direct coupling utilizing a mixed magnesium halide complex | |
| RU2635659C1 (en) | Method of producing benzil ether derivatives of 2-aminonicotinic acid | |
| JPH02138148A (en) | Production of optically active 2-phenoxybutanoic acid | |
| JP4032861B2 (en) | Process for producing β-oxonitrile derivative or alkali metal salt thereof | |
| JPH0136818B2 (en) | ||
| JPS6344746B2 (en) | ||
| KR100311949B1 (en) | Process for the preparation of 1-[(cyclopent-3-en-1-yl)methyl]-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione | |
| SU978724A3 (en) | Method of producing 1-(2,6-dimethylphenoxy)-2-azide-propane | |
| JP3646224B2 (en) | Method for producing benzoylacetonitrile derivative | |
| JP2809481B2 (en) | 2-Alkoxycarbonyl-3-pyridinecarboxylic acid derivatives, their production and herbicides | |
| JP2716243B2 (en) | N-benzyl-3-hydroxysuccinamic acid and method for producing the same | |
| US5290944A (en) | Method for producing dichloromethylpyridines | |
| JPH10120674A (en) | Production of 2-methyl-3-(3,4-methylenedioxyphenyl) acrylic aldehyde | |
| JP3376481B2 (en) | Method for producing hexahydropyridazine | |
| JP2809483B2 (en) | 6-Indolizinecarboxamide derivatives, intermediates thereof, methods for their preparation and herbicides | |
| FI82442B (en) | Process for preparing a 2-arylpropionic acid-magnesium halide complex, and its use for preparing 2-arylpropionic acid | |
| WO1995021828A1 (en) | Process for producing hexahydropyridazine and hexahydropyridazine-1,2-dicarboxylate derivative | |
| JPS62120350A (en) | Manufacture of glycol amides | |
| SE430155B (en) | SET TO MAKE 2-ARYLPROPIONIC ACIDS | |
| JPS62267267A (en) | Pyrazole derivative and production thereof | |
| CA3135512A1 (en) | Method for preparing 2-arylmalonic acid derivative and intermediate, and use thereof | |
| JPH07133271A (en) | Banzaldehyde derivative and production of chromancarboxylic acid derivative using the same as intermediate | |
| JPS6277371A (en) | Fluorine-containing pyrazole derivative | |
| JPH0324045A (en) | Manufacture of anilinofumarate through chloromalate or chlorofumarate or their mixture |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20071004 Year of fee payment: 12 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20081004 Year of fee payment: 13 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091004 Year of fee payment: 14 |
|
| EXPY | Cancellation because of completion of term | ||
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091004 Year of fee payment: 14 |