JPS6316374B2 - - Google Patents
Info
- Publication number
- JPS6316374B2 JPS6316374B2 JP6274680A JP6274680A JPS6316374B2 JP S6316374 B2 JPS6316374 B2 JP S6316374B2 JP 6274680 A JP6274680 A JP 6274680A JP 6274680 A JP6274680 A JP 6274680A JP S6316374 B2 JPS6316374 B2 JP S6316374B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- halogeno
- reaction
- phenylpropionitrile
- present
- 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.)
- Expired
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
- 239000011707 mineral Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- 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 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 235000010755 mineral Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ACRWYXSKEHUQDB-UHFFFAOYSA-N 3-phenylpropionitrile Chemical compound N#CCCC1=CC=CC=C1 ACRWYXSKEHUQDB-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ZUPBNBYEVVGQKK-UHFFFAOYSA-N 2-chloro-3-phenylpropanenitrile Chemical compound N#CC(Cl)CC1=CC=CC=C1 ZUPBNBYEVVGQKK-UHFFFAOYSA-N 0.000 description 2
- LIDRHDRWTSPELB-UHFFFAOYSA-N 2-chloro-3-phenylpropanoic acid Chemical compound OC(=O)C(Cl)CC1=CC=CC=C1 LIDRHDRWTSPELB-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZCCNNBFUMWEZGE-UHFFFAOYSA-N 2-bromo-3-phenylpropanenitrile Chemical compound N#CC(Br)CC1=CC=CC=C1 ZCCNNBFUMWEZGE-UHFFFAOYSA-N 0.000 description 1
- WDRSCFNERFONKU-UHFFFAOYSA-N 2-bromo-3-phenylpropanoic acid Chemical compound OC(=O)C(Br)CC1=CC=CC=C1 WDRSCFNERFONKU-UHFFFAOYSA-N 0.000 description 1
- COFLEEXNUWNKKA-UHFFFAOYSA-N 2-chloro-2-phenylpropanenitrile Chemical compound N#CC(Cl)(C)C1=CC=CC=C1 COFLEEXNUWNKKA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 238000007192 Meerwein reaction reaction Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
本発明は、α−ハロゲノ−β−フエニルプロピ
オン酸の製造法に関するものであり、更に詳しく
はα−ハロゲノ−β−フエニルプロピオニトリル
を加水分解してα−ハロゲノ−β−フエニルプロ
ピオン酸を製造する方法に関するものである。
α−ハロゲノ−β−フエニルプロピオン酸は、
例えば、アンモニアでアミノ化すると容易にフエ
ニルアラニンに誘導することができるから、フエ
ニルアラニン製造の中間体として極めて有用な化
合物である。
α−ハロゲノ−β−フエニルプロピオン酸を製
造する方法としては、α−クロル−β−フエニル
プロピオニトリルを85％ギ酸と濃塩酸で反応させ
る方法が知られている（A.V.Dombrovskiyら；
Zhur.Obshchey Khim.、27、3346−９（1957）：
Ca52、9019i（1958））。しかし、この方法では還
流という激しい条件下で10時間もの長時間反応を
行なわせている。
本発明者らは、α−ハロゲノ−β−フエニルプ
ロピオニトリルの酸性水溶液中での加水分解反応
について鋭意研究した結果、α−ハロゲノ−β−
フエニルプロピオニトリルを鉱酸と酢酸またはプ
ロピオン酸の存在下で加水分解すると反応は温和
な条件下で極めて速く完結することを見出して本
発明を完成した。従つて、本発明は、α−ハロゲ
ノ−β−フエニルプロピオニトリルを鉱酸および
酢酸または鉱酸およびプロピオン酸の存在下で加
水分解することを特徴とするα−ハロゲノ−β−
フエニルプロピオン酸の製造法を提供するもので
ある。
本発明の方法で原料として使用するα−ハロゲ
ノ−β−フエニルプロピオニトリルは、例えば、
アニリンから誘導されるベンゼンジアゾニウム塩
とアクリロニトリルを塩化第二銅の存在下で反応
させる、いわゆるメールヴアイン（Meerwein）
反応により容易に製造することができる。
本発明の方法では、鉱酸として塩酸、硫酸、臭
化水素酸等を使用しうる。その使用量は、α−ハ
ロゲノ−β−フエニルプロピオニトリル１モルに
対して約１モル量以上であり、好ましくは約1.5
モルから約10モルである。又、反応系中には反応
の化学量論から要求される量以上の水が存在する
ことが必要である。通常は化学量論量の１ないし
約10倍量程度を用いる。
酢酸又はプロピオン酸の使用量については、格
別の限定はないが、原料と鉱酸が均一に溶解する
程度の量が好ましい。通常はα−ハロゲノ−β−
フエニルプロピオニトリル１モルに対して約10モ
ルないし約100モル程度である。酢酸およびプロ
ピオン酸は、反応を加速するだけでなく、反応溶
媒としても役立つ。
反応温度は低温では反応し難く、高温では原料
および生成物の分解する傾向があるので、約30℃
以上、好ましくは約50℃ないし約110℃である。
反応時間は、反応温度等により変りうるが、通常
約30分ないし、約８時間程度である。反応終了
後、生成したα−ハロゲノ−β−フエニルプロピ
オン酸は、公知の手段で単離精製することができ
る。例えば、反応混合液から揮発分を留去したの
ち、これを有機溶媒で抽出し、有機相を水で洗浄
乾燥し、溶媒を留去すれば、α−ハロゲノ−β−
フエニルプロピオン酸をうることができる。
本発明によれば、α−ハロゲノ−β−フエニル
プロピオニトリルからα−ハロゲノ−β−フエニ
ルプロピオン酸を極めて短時間のうちに収率よく
製造することができる。その際、副反応はほとん
ど起らない。
以下実施例により本発明を更に詳しく説明する
が、本発明はこれらの実施例に限定されるもので
はない。
実施例 １
α−クロル−α−フエニルプロピオニトリル
4.97ｇ（0.03モル）に酢酸20mlおよび濃塩酸9.12
ｇ（0.09モル）を加え、撹拌しながら100℃で１
時間反応させた。反応後、反応液を蒸留し、残分
をベンゼン50mlで抽出した。
このベンゼン相を水で２回洗浄、無水硫酸マグ
ネシウム上で乾燥させた後、ベンゼンを留去して
油状物を得た。これを室温で一夜放置したところ
結晶化した（得量5.23ｇ、収率91.4％）。この結
晶をｎ−ヘキサンから再結晶してα−クロル−β
−フエニルプロピオン酸の結晶4.81ｇを得た（収
率86.8％）。得られた結晶の融点および元素分析
値は下記の通りであつた。
融 点 48〜50℃
元素分析値 C9H9ClO2として
理論値 Ｃ 58.55 Ｈ 4.91 Cl 19.20
実験値 Ｃ 58.37 Ｈ 4.81 Cl 19.31
実施例 ２
α−ブロム−β−フエニルプロピオニトリル
6.30ｇ（0.03モル）にプロピオン酸40mlおよび濃
塩酸9.12ｇ（0.09モル）を加え、撹拌しながら
100℃で１時間反応させた。反応後、反応液を蒸
留し、残分をベンゼン50mlで抽出した。このベン
ゼン相を水で２回洗浄し、無水硫酸マグネシウム
上で乾燥させた後、ベンゼンを留去し、α−ブロ
ム−β−フエニルプロピオン酸6.41ｇを油状物と
して得た（収率93.20％）。
元素分析値 C9H9BrO2として
理論値 Ｃ 47.19 Ｈ 3.96 Br 34.88
実験値 Ｃ 47.25 Ｈ 3.92 Br 34.69
実施例 ３〜５
α−クロル−β−フエニルプロピオニトリル
2.0ｇ（12ミリモル）に鉱酸又は鉱酸および水な
らびに酢酸20mlを加え、以下第１表に示す温度
で、かつ、同表に示す時間の間反応させた。反応
液を実施例１に準じて処理し、第１表に示す収量
および収率でα−クロル−β−フエニルプロピオ
ン酸を得た。
The present invention relates to a method for producing α-halogeno-β-phenylpropionic acid, and more specifically to a method for producing α-halogeno-β-phenylpropionic acid by hydrolyzing α-halogeno-β-phenylpropionitrile. The present invention relates to a method for producing acid. α-halogeno-β-phenylpropionic acid is
For example, it can be easily derived into phenylalanine by amination with ammonia, so it is an extremely useful compound as an intermediate for the production of phenylalanine. As a method for producing α-halogeno-β-phenylpropionic acid, a method is known in which α-chloro-β-phenylpropionitrile is reacted with 85% formic acid and concentrated hydrochloric acid (AVDombrovskiy et al.;
Zhur. Obshchey Khim., 27 , 3346-9 (1957):
Ca 52 , 9019i (1958)). However, this method requires a long reaction time of 10 hours under intense reflux conditions. As a result of intensive research on the hydrolysis reaction of α-halogeno-β-phenylpropionitrile in an acidic aqueous solution, the present inventors found that α-halogeno-β-phenylpropionitrile
The present invention was completed based on the discovery that when phenylpropionitrile is hydrolyzed in the presence of a mineral acid and acetic acid or propionic acid, the reaction is completed extremely quickly under mild conditions. Therefore, the present invention provides α-halogeno-β-phenylpropionitrile, which is characterized by hydrolyzing α-halogeno-β-phenylpropionitrile in the presence of a mineral acid and acetic acid or a mineral acid and propionic acid.
A method for producing phenylpropionic acid is provided. α-halogeno-β-phenylpropionitrile used as a raw material in the method of the present invention is, for example,
The so-called Meerwein reaction of a benzenediazonium salt derived from aniline with acrylonitrile in the presence of cupric chloride
It can be easily produced by reaction. In the method of the present invention, hydrochloric acid, sulfuric acid, hydrobromic acid, etc. can be used as the mineral acid. The amount used is about 1 mol or more, preferably about 1.5 mol per mol of α-halogeno-β-phenylpropionitrile.
moles to about 10 moles. Furthermore, it is necessary that water be present in the reaction system in an amount greater than that required from the stoichiometry of the reaction. Usually, an amount of 1 to about 10 times the stoichiometric amount is used. The amount of acetic acid or propionic acid to be used is not particularly limited, but is preferably an amount that allows the raw material and the mineral acid to be uniformly dissolved. Usually α-halogeno-β-
The amount is about 10 mol to about 100 mol per mol of phenylpropionitrile. Acetic acid and propionic acid not only accelerate the reaction, but also serve as reaction solvents. The reaction temperature is approximately 30℃, as it is difficult to react at low temperatures, and the raw materials and products tend to decompose at high temperatures.
The temperature is preferably about 50°C to about 110°C.
The reaction time may vary depending on the reaction temperature, etc., but is usually about 30 minutes to about 8 hours. After completion of the reaction, the produced α-halogeno-β-phenylpropionic acid can be isolated and purified by known means. For example, by distilling off volatile components from the reaction mixture, extracting it with an organic solvent, washing the organic phase with water, drying, and distilling off the solvent, α-halogen-β-
Phenylpropionic acid can be obtained. According to the present invention, α-halogeno-β-phenylpropionic acid can be produced from α-halogeno-β-phenylpropionitrile in a very short time with good yield. At that time, almost no side reactions occur. The present invention will be explained in more detail below with reference to Examples, but the present invention is not limited to these Examples. Example 1 α-chloro-α-phenylpropionitrile
4.97g (0.03mol) with 20ml of acetic acid and 9.12ml of concentrated hydrochloric acid
g (0.09 mol) and heated to 100°C with stirring.
Allowed time to react. After the reaction, the reaction solution was distilled and the residue was extracted with 50 ml of benzene. This benzene phase was washed twice with water, dried over anhydrous magnesium sulfate, and then benzene was distilled off to obtain an oil. When this was left overnight at room temperature, it crystallized (obtained amount: 5.23 g, yield: 91.4%). This crystal was recrystallized from n-hexane to form α-chloro-β.
-4.81 g of crystals of phenylpropionic acid were obtained (yield: 86.8%). The melting point and elemental analysis values of the obtained crystals were as follows. Melting point 48-50℃ Elemental analysis value C 9 H 9 ClO 2 Theoretical value C 58.55 H 4.91 Cl 19.20 Experimental value C 58.37 H 4.81 Cl 19.31 Example 2 α-bromo-β-phenylpropionitrile
Add 40 ml of propionic acid and 9.12 g (0.09 mol) of concentrated hydrochloric acid to 6.30 g (0.03 mol), and add while stirring.
The reaction was carried out at 100°C for 1 hour. After the reaction, the reaction solution was distilled and the residue was extracted with 50 ml of benzene. This benzene phase was washed twice with water and dried over anhydrous magnesium sulfate, and then benzene was distilled off to obtain 6.41 g of α-bromo-β-phenylpropionic acid as an oil (yield 93.20%). ). Elemental analysis value C 9 H 9 BrO 2 Theoretical value C 47.19 H 3.96 Br 34.88 Experimental value C 47.25 H 3.92 Br 34.69 Examples 3 to 5 α-chloro-β-phenylpropionitrile
Mineral acid or mineral acid and water and 20 ml of acetic acid were added to 2.0 g (12 mmol) and reacted at the temperature shown in Table 1 below and for the time shown in the same table. The reaction solution was treated according to Example 1 to obtain α-chloro-β-phenylpropionic acid in the yield shown in Table 1.
【表】
なお、得られたα−クロル−β−フエニルプロ
ピオン酸の同定および収率の確認は高速液体クロ
マトグラフイーで行なつた。
高速液体クロマトグラフイー分析の測定装置お
よび測定条件は下記のとおりである。
装 置：高速クロマトグラフ（東洋曹達工業株
式会社製、「TSK HLC802」．商標）
カラム：内径7.5mm×長さ200mm
充填剤：TSK GEL LS−170〔商標 東洋曹達
工業(株)製〕（5μ）
溶離液：酢酸ナトリウム水溶液（0.8重量％）
流 速：0.8ml／分
測定温度：25℃
検出器：UV254nｍ[Table] Note that the identification and yield of the obtained α-chloro-β-phenylpropionic acid were performed by high performance liquid chromatography. The measurement equipment and measurement conditions for high performance liquid chromatography analysis are as follows. Equipment: High-speed chromatograph (manufactured by Toyo Soda Kogyo Co., Ltd., "TSK HLC802". Trademark) Column: Inner diameter 7.5 mm x length 200 mm Packing material: TSK GEL LS-170 [Trademark made by Toyo Soda Kogyo Co., Ltd.] (5μ ) Eluent: Sodium acetate aqueous solution (0.8% by weight) Flow rate: 0.8ml/min Measurement temperature: 25℃ Detector: UV254nm
Claims (1)
−ハロゲノ−β−フエニルプロピオニトリルを鉱
酸および酢酸または鉱酸およびプロピオン酸の存
在下で加水分解することを特徴とする一般式 （Ｘは上記Ｘと同じ意味を表わす）で示されるα
−ハロゲノ−β−フエニルプロピオン酸の製造
法。 ２ 反応を温度約50℃ないし約110℃で行う特許
請求の範囲第１項記載の製造法。[Claims] 1. General formula α represented by (in the formula, X represents a halogen atom)
General formula characterized in that - halogeno-β-phenylpropionitrile is hydrolyzed in the presence of a mineral acid and acetic acid or a mineral acid and propionic acid. α denoted by (X has the same meaning as X above)
-Production method of halogeno-β-phenylpropionic acid. 2. The manufacturing method according to claim 1, wherein the reaction is carried out at a temperature of about 50°C to about 110°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6274680A JPS56158732A (en) | 1980-05-14 | 1980-05-14 | Preparation of alpha-halogeno-beta-phenylpropionic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6274680A JPS56158732A (en) | 1980-05-14 | 1980-05-14 | Preparation of alpha-halogeno-beta-phenylpropionic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56158732A JPS56158732A (en) | 1981-12-07 |
| JPS6316374B2 true JPS6316374B2 (en) | 1988-04-08 |
Family
ID=13209264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6274680A Granted JPS56158732A (en) | 1980-05-14 | 1980-05-14 | Preparation of alpha-halogeno-beta-phenylpropionic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56158732A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6081144A (en) * | 1983-10-13 | 1985-05-09 | Toyo Soda Mfg Co Ltd | Production of alpha-halogeno-beta-phenylpropionic acid |
| US4983758A (en) * | 1987-12-03 | 1991-01-08 | Sumitomo Chemical Company, Limited | Process for producing an optically active α-isopropyl-p-chlorophenylacetic acid |
| IT1298268B1 (en) * | 1998-02-18 | 1999-12-20 | Zambon Spa | PROCEDURE FOR THE PREPARATION OF THE (S) -2-BROMO-3-PHENYL-PROPIONIC ACID |
-
1980
- 1980-05-14 JP JP6274680A patent/JPS56158732A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56158732A (en) | 1981-12-07 |
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