JPS63174952A - Production of high-purity 2-(4-hydroxyphenoxy)propionic ester - Google Patents
Production of high-purity 2-(4-hydroxyphenoxy)propionic esterInfo
- Publication number
- JPS63174952A JPS63174952A JP793087A JP793087A JPS63174952A JP S63174952 A JPS63174952 A JP S63174952A JP 793087 A JP793087 A JP 793087A JP 793087 A JP793087 A JP 793087A JP S63174952 A JPS63174952 A JP S63174952A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyphenoxy
- propionic acid
- bis
- purity
- acid containing
- 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
- 238000004519 manufacturing process Methods 0.000 title description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 title 1
- 239000002904 solvent Substances 0.000 claims abstract description 16
- AQIHDXGKQHFBNW-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000001953 recrystallisation Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 16
- -1 hydroxyphenoxy Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000003151 propanoic acid esters Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 4
- 235000019260 propionic acid Nutrition 0.000 abstract description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract description 4
- 239000004009 herbicide Substances 0.000 abstract description 3
- SSGKBOVUWGMTBK-UHFFFAOYSA-N 2-[4-(1-carboxyethoxy)phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(OC(C)C(O)=O)C=C1 SSGKBOVUWGMTBK-UHFFFAOYSA-N 0.000 abstract description 2
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000005599 propionic acid derivatives Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- UBQVNWGAGGMGCX-UHFFFAOYSA-N 4-prop-1-en-2-yloxyphenol Chemical group C1(O)=CC=C(OC(=C)C)C=C1 UBQVNWGAGGMGCX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PQKBPHSEKWERTG-UHFFFAOYSA-N Fenoxaprop ethyl Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- NUKZAGXMHTUAFE-UHFFFAOYSA-N hexanoic acid methyl ester Natural products CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、高純度の２−（４−ヒドロキシフエノキシ）
プロピオン酸エステルの製法に関する。本発明の方法で
得られる化合物は各種の７二ノキシプロピオン酸系除草
剤の合成中間体として有用である。即ち本発明の方法で
得られる高純度な２−（４−ヒドロキシフエノキシ）プ
ロピオン酸エステルは例えば、フルアジホップブチル、
キノホップエチル、ジクロホップメチル、トリホップメ
チル及びフェノキサプロップエチルなどの中間体として
有用に使用することが出来るものである。Detailed Description of the Invention (Industrial Application Field) The present invention provides highly purified 2-(4-hydroxyphenoxy)
This invention relates to a method for producing propionic acid ester. The compounds obtained by the method of the present invention are useful as synthetic intermediates for various 7dinoxypropionic acid herbicides. That is, the highly pure 2-(4-hydroxyphenoxy)propionic acid ester obtained by the method of the present invention includes, for example, fluazifopbutyl,
It can be usefully used as an intermediate for quinofop-ethyl, diclofop-methyl, triphop-methyl, fenoxaprop-ethyl, and the like.
（従来技術およびその問題点）
２−（４−ヒドロキシフエノキシ）プロピオン酸エステ
ルの製造法については、多くの公知例が知られている。(Prior Art and its Problems) Many known examples are known of methods for producing 2-(4-hydroxyphenoxy)propionic acid esters.
例えば特開昭５４−１９９２５．５６−５９７１８．５
８−１８３６６６．５９−９５２３７．６０−９４９３
５．６０−２０４７４５．６〇−２０９５４８，６１−
１０９７５３，６１−１５８９４７などを挙げることが
出来る。しかしながら上記方法はいずれもハイドロキノ
ンと対応するプロピオン酸誘導体との反応により目的物
を得る方法であり、目的のハイドロキノンモノ置換体の
外に不要なビス置換体の副生を伴うという問題点がある
。モノ置換体を選択的に得るための試みも幾つか知られ
ている（例えば特開昭５９−２３１０４４、アメリカ特
許４３６８０６８、公表公報昭５７−５０１１７８、特
開昭６Ｏ−８１１５０）。これらの方法はいずれも形式
的にはハイドロキノンの一方を保護した上でプロピオン
酸誘導体と反応させた後に保護基を除去するという方゛
式を採用している。For example, JP-A-54-19925.56-59718.5
8-183666.59-95237.60-9493
5.60-204745.6〇-209548,61-
109753, 61-158947, etc. However, all of the above methods obtain the desired product by reacting hydroquinone with the corresponding propionic acid derivative, and there is a problem in that in addition to the desired hydroquinone monosubstituted product, unnecessary bis-substituted products are produced as by-products. Some attempts to selectively obtain monosubstituted products are known (for example, JP-A-59-231044, US Pat. No. 4,368,068, Publication No. 57-501178, JP-A-6O-81150). All of these methods formally employ a method in which one side of the hydroquinone is protected, reacted with a propionic acid derivative, and then the protecting group is removed.
従って上記方法では保護基の導入及び除去と言った繁雑
な工程を経なければならない。また目的化合物が光学活
性体の場合にあっては、いずれの方法においても光学純
度は必ずしも満足いくものではなかった。光学的に純粋
な化合物を得ようとすれば、例えば特開昭６１−８３１
４４の如くジアステレオマー法による光学分割操作を何
度か繰り返す必要があった。以上の様に従来技術におい
ては、工業的有利に化学的及び光学的に高純度な２−（
４−ヒドロキシフエノキシ）プロピオン酸エステルを得
ることは困難であった。Therefore, the above method requires complicated steps such as introduction and removal of protecting groups. Furthermore, when the target compound is an optically active substance, the optical purity is not necessarily satisfactory in any of the methods. If you want to obtain an optically pure compound, for example, JP-A-61-831
It was necessary to repeat the optical resolution operation using the diastereomer method several times as in No. 44. As described above, in the prior art, 2-(
It was difficult to obtain 4-hydroxyphenoxy)propionic acid ester.
（問題点を解決するための手段）
本発明の目的は、除草剤中間体として有望な高純度２−
（４−ヒドロキシフエノキシ）プロピオン酸エステルを
上記の種々の問題点を改善し効率的に得る方法を提供す
ることにある。即ち本発明は、１，４−ビス（１−カル
ボキシエトキシ）ベンゼン（以下ビス置換体という）を
含む２−（４−ヒドロキシフエノキシ）プロピオン酸を
再結晶し、次いでエステル化することを特徴とする高純
度２−（４−ヒドロキシフエノキシ）プロピオン酸エス
テルの製法に関するものである。本発明の方法で用いら
れるビス置換体を含む２−（４−ヒドロキシフエノキシ
）プロピオン酸は、従来技術の公知例で示した如くハイ
ドロキノンとプロピオン酸誘導体との反応生成物から導
くことができる。更に詳しくは本発明の対象とする２−
（４−ヒドロキシフエノキシ）プロピオン酸は、ビス置
換体が３０％以内の範囲で含まれ、又光学活性体にあっ
ては、その光学純度が９５％ｅｅ（エナンチオエキセス
）以下である化合物である。本発明で使用できる溶媒と
してはハロゲン系溶媒、エステル系溶媒芳香族溶媒、ア
ルコール系溶媒、カルボン系溶媒、カルボン酸系溶媒及
び水など様々な溶媒を利用することができる。ハロゲン
系溶媒としてはメチレンクロリド、クロロホルム、１，
２−ジクロルエタン、１，１゜２．２．−テトラクロル
エタンが例示でき、エステル系溶媒としては酢酸エチル
、酢酸メチル、酢酸ブチル、プロピオン酸メチル等が例
示できる。アルコール系溶媒としては、メタノール、エ
タノール、ｎ−プロパツール、イソプロパツール、ｎ−
７’タノール、イ・へブタノール、ｔ−ブタノール等が
例示できる。また炭化水素系溶媒としてはベンゼン、ト
ルエン、キシレン等が例示でき、カルボン酸系溶媒とし
てはギ酸、酢酸、プロピオン酸等が例示できる。しかし
ながら拳法で用いられる再結晶溶媒の種類及び量は特に
限定するものでなく、又２種類以上の混合溶媒も用いら
れる。(Means for Solving the Problems) The object of the present invention is to obtain high-purity 2-
The object of the present invention is to provide a method for efficiently obtaining (4-hydroxyphenoxy)propionic acid ester by improving the various problems mentioned above. That is, the present invention is characterized in that 2-(4-hydroxyphenoxy)propionic acid containing 1,4-bis(1-carboxyethoxy)benzene (hereinafter referred to as bis-substituted product) is recrystallized and then esterified. The present invention relates to a method for producing high-purity 2-(4-hydroxyphenoxy)propionic acid ester. The bis-substituted 2-(4-hydroxyphenoxy)propionic acid used in the process of the invention can be derived from the reaction product of hydroquinone with a propionic acid derivative as shown in the known examples of the prior art. . More specifically, 2-
(4-Hydroxyphenoxy)propionic acid is a compound that contains bis-substituted products within 30% and, in the case of optically active forms, has an optical purity of 95% ee (enantioexcess) or less. It is. Various solvents that can be used in the present invention include halogen solvents, ester solvents, aromatic solvents, alcohol solvents, carboxyl solvents, carboxylic acid solvents, and water. Examples of halogenated solvents include methylene chloride, chloroform, 1,
2-dichloroethane, 1,1°2.2. -Tetrachloroethane is an example, and examples of ester solvents include ethyl acetate, methyl acetate, butyl acetate, and methyl propionate. Examples of alcoholic solvents include methanol, ethanol, n-propanol, isopropanol, n-
Examples include 7'tanol, i-hebutanol, and t-butanol. Further, examples of hydrocarbon solvents include benzene, toluene, xylene, etc., and examples of carboxylic acid solvents include formic acid, acetic acid, propionic acid, etc. However, the type and amount of the recrystallization solvent used in Kenpo is not particularly limited, and a mixed solvent of two or more types may also be used.
本発明の方法を工程を追って説明すると、上記のビス置
換体を含む２−（４−ヒドロキシフエノキシ）プロピオ
ン酸を上記に例示した溶媒に室温下で加え徐々に加熱昇
温する。加熱温度は用いる溶媒の沸点や溶解度或いは量
により異＆るが概ね５０’Ｃから、１５０°Ｃの範囲が
好適である。この際必要であれば脱色のための活性炭を
適当量加えても良く、上記温度を保ち熱時ろ過により除
去できる。この様にして得られた澄明な溶液を約３０分
から数時間かけて０°Ｃから室温まで徐冷し、析出した
結晶をろ過分離すことにより高純度の２−（４−ヒドロ
キシフエノキシ）プロピオン酸を得ることができる。こ
の様にして得られた高純度２−（４−ヒドロキシフエノ
キシ）プロピオン酸は常法に従ってエステル化され対応
するエステルに導く事ができる。To explain the method of the present invention step by step, the above bis-substituted 2-(4-hydroxyphenoxy)propionic acid is added to the above-mentioned solvent at room temperature and the temperature is gradually increased. The heating temperature varies depending on the boiling point, solubility, and amount of the solvent used, but is preferably in the range of approximately 50'C to 150°C. At this time, if necessary, an appropriate amount of activated carbon may be added for decolorization, and it can be removed by filtration while hot while maintaining the above temperature. The clear solution thus obtained is gradually cooled from 0°C to room temperature over a period of about 30 minutes to several hours, and the precipitated crystals are separated by filtration to obtain highly pure 2-(4-hydroxyphenoxy). Propionic acid can be obtained. The highly purified 2-(4-hydroxyphenoxy)propionic acid thus obtained can be esterified to the corresponding ester by a conventional method.
（発明の効果）
光学活性な２−（４−ヒドロキシフエノキシ）プロピキ
淋ることが明らかになった。プロピオン酸系除草剤はＬ
体に比べ０体の除草活性が大きいことが知られており、
拳法を用いれば０体の２−（４−ヒドロキシフエノキシ
）プロピＡエステルを高い光学純度で得ることも出来る
。(Effects of the Invention) It has been revealed that optically active 2-(4-hydroxyphenoxy) propylene is isolated. Propionic acid herbicide L
It is known that the herbicidal activity of 0 body is greater than that of 0 body,
By using Kenpo, it is also possible to obtain 0-body 2-(4-hydroxyphenoxy)propyl A ester with high optical purity.
実施例１
３％（光学純度９１．０％ｅｅ）、ビス置換体１０．７
％、その他有機物１．１％、灰分３．２％、水分１．７
％月１０．０ｇに水１０ミリリットルを加え、８０°Ｃ
まで加熱し溶解した。室温下で空冷し約１時間放置した
。析出した結晶をろ過分離し乾燥したところ、７．３６
ｇの２−（４−ヒドロキシフエノキシ）プロピ？％ （
［Ｑ］ ’Ｑ” ＋５８．７（Ｃ＝１．００、アセトン
））が得られた。更に常法に従いメチルエステル化する
ことにより２−（４−ヒドロキシフエノキシフロヒオン
酸メチルカフ、７７ｇ（［α］ｖ＋４３．３（Ｃ＝１．
６０、クロロホルム））得られた。このものの分析値を
以下に示す。Example 1 3% (optical purity 91.0%ee), bis-substituted product 10.7
%, other organic matter 1.1%, ash 3.2%, moisture 1.7
Add 10ml of water to 10.0g of %month and heat to 80°C.
It was heated until it dissolved. The mixture was air-cooled at room temperature and left for about 1 hour. When the precipitated crystals were separated by filtration and dried, the result was 7.36
g of 2-(4-hydroxyphenoxy)propy? % (
[Q] 'Q'' +58.7 (C=1.00, acetone)) was obtained. Further, by methyl esterification according to a conventional method, 77 g of methyl 2-(4-hydroxyphenoxyfluorohionate cuff) was obtained ( [α]v+43.3 (C=1.
60, chloroform)) was obtained. The analytical values for this product are shown below.
２−（４−ヒドロキシフエノキシ） ９８．３％−プ
ロピオン酸メチル （光学純度９８．９％ｅｅ）
ビス置換体 １．３％その他有機物
０．４％
組成比はガスクロマトグラフィにより決定した。Methyl 2-(4-hydroxyphenoxy) 98.3%-propionate (optical purity 98.9%ee)
Bis-substituted product 1.3% other organic matter
0.4% The composition ratio was determined by gas chromatography.
又光学純度は光学分割カラムを用い決定した。Furthermore, optical purity was determined using an optical resolution column.
実施例２〜６
実施例１において２−（４−ヒドロキシフエノキシ）プ
ロピ八とビス置換体の組成比が９６．９ ： ３．１で
あり、溶媒及び溶媒の批をがえた他は実施例１と同様の
方法を行ったその結果を表１に示す。Examples 2 to 6 Example 1 was carried out except that the composition ratio of 2-(4-hydroxyphenoxy)propyl and bis-substituted product was 96.9:3.1, and the solvent and the solvent were changed. The same method as in Example 1 was carried out and the results are shown in Table 1.
Claims (3)
ンを含む２−（４−ヒドロキシフエノキシ）プロピオン
酸を再結晶し、次いでエステル化する事を特徴とする高
純度２−（４−ヒドロキシフエノキシ）プロピオン酸エ
ステルの製法。(1) Highly purified 2-(4- Process for producing hydroxyphenoxy)propionic acid ester.
範囲第一項記載の方法。(2) The method according to claim 1, wherein the recrystallization solvent is water.
エステルが光学活性体である事を特徴とする特許請求の
範囲第一項及び第二項記載の方法。(3) The method according to claims 1 and 2, wherein the 2-(4-hydroxyphenoxy)propionic acid ester is an optically active ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP793087A JPS63174952A (en) | 1987-01-16 | 1987-01-16 | Production of high-purity 2-(4-hydroxyphenoxy)propionic ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP793087A JPS63174952A (en) | 1987-01-16 | 1987-01-16 | Production of high-purity 2-(4-hydroxyphenoxy)propionic ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63174952A true JPS63174952A (en) | 1988-07-19 |
Family
ID=11679241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP793087A Pending JPS63174952A (en) | 1987-01-16 | 1987-01-16 | Production of high-purity 2-(4-hydroxyphenoxy)propionic ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63174952A (en) |
-
1987
- 1987-01-16 JP JP793087A patent/JPS63174952A/en active Pending
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