JPS62238234A - Production of 2-(3-benzoylphenyl)propionic acid - Google Patents
Production of 2-(3-benzoylphenyl)propionic acidInfo
- Publication number
- JPS62238234A JPS62238234A JP8264586A JP8264586A JPS62238234A JP S62238234 A JPS62238234 A JP S62238234A JP 8264586 A JP8264586 A JP 8264586A JP 8264586 A JP8264586 A JP 8264586A JP S62238234 A JPS62238234 A JP S62238234A
- Authority
- JP
- Japan
- Prior art keywords
- benzoylphenyl
- peroxide
- formula
- propionic acid
- pentanedione
- 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
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000002978 peroxides Chemical class 0.000 claims abstract description 8
- 238000006462 rearrangement reaction Methods 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 6
- JFMLICWPWKXNJT-UHFFFAOYSA-N 1-(3-benzoylphenyl)propan-2-one Chemical compound CC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 JFMLICWPWKXNJT-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- NYSDOTODQRZVMW-UHFFFAOYSA-N 3-(3-benzoylphenyl)pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 NYSDOTODQRZVMW-UHFFFAOYSA-N 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- -1 j-tanol Chemical compound 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 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 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- IRYIYPWRXROPSX-UHFFFAOYSA-N 3-(1-cyanoethyl)benzoic acid Chemical compound N#CC(C)C1=CC=CC(C(O)=O)=C1 IRYIYPWRXROPSX-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 108010032976 Enfuvirtide Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ZJRXSAYFZMGQFP-UHFFFAOYSA-N barium peroxide Chemical compound [Ba+2].[O-][O-] ZJRXSAYFZMGQFP-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- PEASPLKKXBYDKL-FXEVSJAOSA-N enfuvirtide Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(C)=O)[C@@H](C)O)[C@@H](C)CC)C1=CN=CN1 PEASPLKKXBYDKL-FXEVSJAOSA-N 0.000 description 1
- 229960002062 enfuvirtide Drugs 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N ethyl methyl diketone Natural products CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004972 metal peroxides Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 239000003440 toxic substance 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
本発明は消炎鎮痛作用を有する医薬品として知られる２
−（３−ベンゾイルフェニル）プロピオン酸の製凸方法
に関する。[Detailed Description of the Invention] Industrial Field of Use The present invention is a drug known as a drug with anti-inflammatory and analgesic effects.
This invention relates to a method for producing -(3-benzoylphenyl)propionic acid.
従来の技術
従来より２−（３−ベンゾイルフェニル）フロピオン酸
の製造方法としては、たとえば、Ｎ
Ｒはアルキル基を示す、以下同様）を加水分解、脱カル
ボキシル化する方法（特公昭４５−１９２８７）公明４
７−７０２４）
ＣＩ（３
３） ＡｒＣ１１ＣＮを加水分解する方法（特公昭５２
−８：１０１）脱カルボキシル化する方法（特開昭５５
−２４１．１７）などが知られている。Prior Art Conventionally, 2-(3-benzoylphenyl)furopionic acid has been produced by, for example, hydrolyzing and decarboxylating NR (NR represents an alkyl group, the same applies hereinafter) (Japanese Patent Publication No. 19287/1987). Komei 4
7-7024) CI (3 3) Method of hydrolyzing ArC11CN (Special Publication No. 52
-8:101) Method of decarboxylation
-241.17), etc. are known.
発明が解決しようとする問題魚
従来法において、上記の方法１）は工程数が多く、シア
ン化す） ＩＪウムのような猛毒物質を使用する工程を
含む。方法３）では出発原料である２−（３−カルボキ
シフェニル）プロピオニトリルを合成する際に液体アン
モニアを用いる必要があり、また収率も悪い。方法２）
、４）は工程数が多い。このように、従来法は工業的に
不利なので、工業的に有利な２−（３−ベンゾイルフェ
ニル）プロピオン酸の製造方法の開発が望まれている。Problems to be Solved by the Invention In the conventional methods, method 1) described above has a large number of steps and includes a step of using highly toxic substances such as cyanide. Method 3) requires the use of liquid ammonia when synthesizing the starting material 2-(3-carboxyphenyl)propionitrile, and the yield is also poor. Method 2)
, 4) has a large number of steps. As described above, since the conventional method is industrially disadvantageous, it is desired to develop an industrially advantageous method for producing 2-(3-benzoylphenyl)propionic acid.
本発明は式（１）
で表される３−１３−ベンゾイルフェニル）−２，４−
ペンタンジオンを過酸化物の存在下に転位反応させるこ
とを特徴とする式（２）
で表される２−（３−ベンゾイルフェニル）プロピオン
酸の製造方法に関する。以下において、式（ＩＬ（２）
で表される化合物を化合物（１）、（２）という。The present invention relates to 3-13-benzoylphenyl)-2,4- represented by formula (1)
The present invention relates to a method for producing 2-(3-benzoylphenyl)propionic acid represented by formula (2), which comprises subjecting pentanedione to a rearrangement reaction in the presence of a peroxide. In the following, the formula (IL(2)
The compounds represented by these are called compounds (1) and (2).
本発明の実施に際しては、化合物（１）を水または有機
溶媒を含有する溶媒に溶解し、過酸化物を加えて反応さ
せ、化合物（１）の転位反応を行わせることにより、化
合物（２）を得ることができる。In carrying out the present invention, compound (1) is dissolved in water or a solvent containing an organic solvent, and a peroxide is added and reacted to carry out a rearrangement reaction of compound (1) to form compound (2). can be obtained.
過酸化物としては過酸化水素、過酢酸などの過酸化物、
過酸化ナトリウム、過酸化バリウムなどの金属過酸化物
などを例示することができる。Peroxides include hydrogen peroxide, peracetic acid, etc.
Examples include metal peroxides such as sodium peroxide and barium peroxide.
溶媒としては水単独あるいはメタン・ル、ｊ−タノール
、ｔ−ブチルアルコールなどのアルコール類もしくは、
アセトン、ジメキサンなどを含む水混合系溶媒を使用す
ることができる。水混合系溶媒の場合は、とくに水を含
む割合を規定するものではない。工業的に有利に使用で
きるのは水単独の場合である。As a solvent, water alone or alcohols such as methane, j-tanol, t-butyl alcohol, or
Water-based solvents containing acetone, dimexane, etc. can be used. In the case of a water-mixed solvent, there is no particular restriction on the proportion of water contained. Water alone can be used industrially advantageously.
反応は一２０℃から溶媒の還流温度、好ましくは５〜８
０℃の範囲で行われる。反応時間は０４５〜３０時間で
ある。The reaction is carried out at a temperature ranging from -20°C to the reflux temperature of the solvent, preferably from 5 to 8°C.
It is carried out in the range of 0°C. The reaction time is 0.45-30 hours.
過酸化物の使用量としては、過酸化物の種類にもよるが
基質に対して１当量から１０当量程度がよい。好ましく
は１当量から３当債である。The amount of peroxide used is preferably about 1 to 10 equivalents relative to the substrate, although it depends on the type of peroxide. Preferably it is from 1 equivalent to 3 equivalents.
反応生成物は常法によって単離、精製することができる
。例えば反応液をａ縮して、その濃縮物に水を加え、生
成物をジエチルエーテルなどで抽出する。エーテル溶液
をａ縮することによって目的物質の化合物（２）を得る
ことができる。The reaction product can be isolated and purified by conventional methods. For example, the reaction solution is condensed, water is added to the concentrate, and the product is extracted with diethyl ether or the like. Compound (2), which is the target substance, can be obtained by condensing the ether solution.
なお、式（１）の化合物の合成法としては、例えばＣ−
Ｌ、Ｍａｏらの方法に準じて、３−ベンゾイルフェニル
アセトンを五フシ化ホウ素を触媒として、無水酢酸でア
ンル化して合成することができる（Ｃ−Ｌ、 Ｍａｏ
ｅｔ ａｌ、、ジャーナル−オブ・オーガニック・
ケミストリイ（Ｊ、 Ｏｒｇ、 Ｃｈｅｍ、 ）。In addition, as a method for synthesizing the compound of formula (1), for example, C-
According to the method of L, Mao et al., 3-benzoylphenylacetone can be synthesized by unnulating with acetic anhydride using boron pentafuside as a catalyst (C-L, Mao et al.
et al., Journal of Organic
Chemistry (J, Org, Chem, ).
３４ 、 ’１４２５（１９６９＞ ：ｌ （参考例１
）。34, '1425 (1969>: l (Reference example 1
).
以下、実施例および参考例により本発明をさらに詳細に
説明する。Hereinafter, the present invention will be explained in more detail with reference to Examples and Reference Examples.
参考例１
３−ベンゾイルフェニルアセトン１４．３ ｇに無水酢
酸１２．２ｇ、ｐ−トルエンスルホン酸−水塩１．１ｇ
、三フッ化ホウ素ジエチルエーテル錯体１５．１ｍｌを
加え、室温で２０時間反応した。反応液を酢酸す） Ｉ
Ｊウド水溶液２０ Ｑｍｌ （酢酸ナトリウム三水塩２
４．６ ｇを含む）と混合し、４時間加熱還流を行った
。反応液を酢酸エチル１０ Ｑｍｌで２回抽出し、得ら
れた酢酸エチル層を水２０ Ｑｍｌで洗浄後、硫酸マグ
ネシウムで乾燥した。減圧下で溶媒を留去し、得られた
残渣をカラムグロマトグラフィー〔シリカゲル＜８００
ｍ１）、酢酸エチル：ｎ−ヘキ勺ン−１： ９ （Ｖ／
Ｖ）、４１〕にて精製シて１１．４ ｇの３− （３−
ベンゾイルフェニル）−２，４−べ〕／タンジオンを得
た（収率６８．０％）。Reference Example 1 14.3 g of 3-benzoylphenylacetone, 12.2 g of acetic anhydride, 1.1 g of p-toluenesulfonic acid hydrate
, 15.1 ml of boron trifluoride diethyl ether complex was added, and the mixture was reacted at room temperature for 20 hours. acetic acid solution) I
J-ud aqueous solution 20 Qml (sodium acetate trihydrate 2
(containing 4.6 g) and heated under reflux for 4 hours. The reaction solution was extracted twice with 10 Qml of ethyl acetate, and the resulting ethyl acetate layer was washed with 20 Qml of water and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was subjected to column chromatography [silica gel <800
m1), ethyl acetate: n-hexane-1: 9 (V/
V), 41] to obtain 11.4 g of 3- (3-
Benzoylphenyl)-2,4-be]/tandione was obtained (yield 68.0%).
生成物の理化学的性質は下記の通りである。The physicochemical properties of the product are as follows.
ＮＭＲ（ＣＤ（１３）；δ１．９０（６１１，ｓ）、
７．３０〜７．８０（９Ｈ，ｍ）、 １６．５６（ＩＨ
，ｓ）Ｃ＋ａ）ｌ＋ｓ○３として
計算値：Ｃ；７７．１２％、 ｔ（；５．７５％測定
値：Ｃ；７７ＪＯ％、 Ｈ；５．８１％実施例１
３− （３−ベンゾイルフェニル１２．４−ペンタンジ
オン２．８ｇをｔ−ブチルアルコールｌ Ｑｍｌに溶解
し、３５％過酸化水素水３．０ｇ、ｆｉ硫酸１滴を加え
６０℃で４時間攪拌した。反応後水１００ｍ１を加え酢
酸エチル２０ Ｑｍｌで抽出した。抽出液を硫酸マグネ
シウムで乾燥後、減圧下で溶媒を留去１．て、２− （
３−ベンゾイルフェニル）プロピオン酸の結晶２．３９
ｇを得た（収率９４．０％）、。NMR (CD(13); δ1.90(611,s),
7.30-7.80 (9H, m), 16.56 (IH
,s)C+a)l+s○3 Calculated value: C; 77.12%, t(;5.75% Measured value: C; 77JO%, H; 5.81% Example 1 3-(3-benzoylphenyl 12.2.8 g of 4-pentanedione was dissolved in 1 Qml of t-butyl alcohol, 3.0 g of 35% hydrogen peroxide solution and 1 drop of fi sulfuric acid were added, and the mixture was stirred at 60°C for 4 hours. After the reaction, 100 ml of water was added. Extraction was performed with 20 Qml of ethyl acetate. After drying the extract over magnesium sulfate, the solvent was distilled off under reduced pressure.
Crystals of 3-benzoylphenyl)propionic acid 2.39
g (yield 94.0%).
得られた試料をベンゼンと石油エーテル（に６）から再
結晶で精製して理化学的性質を調べた。。The obtained sample was purified by recrystallization from benzene and petroleum ether (6), and its physicochemical properties were investigated. .
結晶化合物の理化学的性質は下記のとおりである。The physicochemical properties of the crystalline compound are as follows.
融点：９３．０〜９４．０℃
ＮＭＲ（ＣＤＣ１，）；δ１．５５ （３Ｈ，ｄ、 Ｊ
＝７Ｈｚ） 。Melting point: 93.0-94.0°C NMR (CDC1,); δ1.55 (3H, d, J
=7Hz).
３、８２ （ＩＨ，ｑ、 Ｊ＝７ｔｌｚ）、７．１５〜
８．００（９Ｈ，ｍ）ｌｆｌ、４０（１１（、ｓ）
Ｃ，、Ｈ，，０３として
計算値、Ｃ；７５．５７％、 Ｈ；５．５５％測定値
：Ｃ；７５．４２％、 Ｈ；５．６８％実施例２
３− （３−ペンゾイルブエニルｉ２．４−ペンタンジ
オン０．２８ ｇに３５％過酸化水素水５ｎ＋ｌ、濃硫
酸１滴を加え３時間加熱還流をした。冷却後水５ｍｌを
加え酢酸エチル（１０ｍｌ、２回）で抽出した。抽出液
を硫酸マグネシウムで乾燥後、減圧下で溶媒を留去して
、２−（３−ベンゾイルフェニル）プロピオン酸の結晶
０．２１ｇを寿だ（収率８２、６％）。ベンゼンと石油
エーテル（１：６）から再結晶して得られた試料の融点
、ＮＭＲスペクトル、元素分析値は実施例１で得られた
ものと一致した。3, 82 (IH, q, J=7tlz), 7.15~
8.00 (9H, m) lfl, 40 (11 (, s) Calculated value as C,, H,,03, C; 75.57%, H; 5.55% Measured value: C; 75.42% , H; 5.68% Example 2 3-(3-Penzoylbuenyl i) To 0.28 g of 2.4-pentanedione were added 5 n+l of 35% hydrogen peroxide solution and 1 drop of concentrated sulfuric acid, and the mixture was heated under reflux for 3 hours. After cooling, 5 ml of water was added and extracted with ethyl acetate (10 ml, twice).The extract was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain crystals of 2-(3-benzoylphenyl)propionic acid. The melting point, NMR spectrum, and elemental analysis values of the sample obtained by recrystallization from benzene and petroleum ether (1:6) were those obtained in Example 1. matched.
発明の効果
本発明によれば、２−（３−ベンゾイルフェニル）プロ
ピオン酸を、収率よく工業的に有利に製造することがで
きる。Effects of the Invention According to the present invention, 2-(3-benzoylphenyl)propionic acid can be industrially advantageously produced in good yield.
Claims (1)
ベンタンジオンを過酸化物の存在下に転位反応させるこ
とを特徴とする式（２） ▲数式、化学式、表等があります▼（２） で表される２−（３−ベンゾイルフェニル）プロピオン
酸の製造方法。[Claims] 3-(3-benzoylphenyl)-2,4- represented by formula (1) ▲Mathematical formulas, chemical formulas, tables, etc.▼(1)
2-(3-benzoylphenyl)propionic acid represented by formula (2) ▲Mathematical formulas, chemical formulas, tables, etc. are available▼(2), which is characterized by rearrangement reaction of betanedione in the presence of peroxide. Production method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8264586A JPS62238234A (en) | 1986-04-10 | 1986-04-10 | Production of 2-(3-benzoylphenyl)propionic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8264586A JPS62238234A (en) | 1986-04-10 | 1986-04-10 | Production of 2-(3-benzoylphenyl)propionic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62238234A true JPS62238234A (en) | 1987-10-19 |
Family
ID=13780164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8264586A Pending JPS62238234A (en) | 1986-04-10 | 1986-04-10 | Production of 2-(3-benzoylphenyl)propionic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62238234A (en) |
-
1986
- 1986-04-10 JP JP8264586A patent/JPS62238234A/en active Pending
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