JPS62263140A - Production of alpha-phenylpropionic acid derivative - Google Patents
Production of alpha-phenylpropionic acid derivativeInfo
- Publication number
- JPS62263140A JPS62263140A JP61106403A JP10640386A JPS62263140A JP S62263140 A JPS62263140 A JP S62263140A JP 61106403 A JP61106403 A JP 61106403A JP 10640386 A JP10640386 A JP 10640386A JP S62263140 A JPS62263140 A JP S62263140A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- oxygen
- containing organic
- solvent
- organic compound
- 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
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical class CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 17
- 239000002904 solvent Substances 0.000 abstract description 11
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 8
- 229930195733 hydrocarbon Natural products 0.000 abstract description 8
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- 150000003623 transition metal compounds Chemical class 0.000 abstract description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract description 4
- 150000003284 rhodium compounds Chemical class 0.000 abstract description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract description 3
- 239000011630 iodine Substances 0.000 abstract description 3
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 230000001747 exhibiting effect Effects 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
- 238000006243 chemical reaction Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000002497 iodine compounds Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- -1 rhodium halide Chemical class 0.000 description 2
- KXAHUXSHRWNTOD-UHFFFAOYSA-K rhodium(3+);triiodide Chemical compound [Rh+3].[I-].[I-].[I-] KXAHUXSHRWNTOD-UHFFFAOYSA-K 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 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 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、α−フェニルプロピオン酸誘導体の工業的製
造法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an industrial method for producing α-phenylpropionic acid derivatives.
α−フェニルプロピオン酸誘導体は、鎮痛、消炎、解熱
等の薬理作用を有し、医薬品として有用−である。α-Phenylpropionic acid derivatives have pharmacological effects such as analgesia, anti-inflammatory, and antipyretic properties, and are useful as pharmaceuticals.
α−フェニルプロピオン酸誘導体の製造法については、
近年数多くの合成経路が提示されているが、何れも、反
応工程が長い、高価である、 ゛あるいは有毒な試
薬を使用するなど工業的に満足すべきものではなかった
。Regarding the production method of α-phenylpropionic acid derivatives,
Many synthetic routes have been proposed in recent years, but none of them are industrially satisfactory, as they require long reaction steps, are expensive, or use toxic reagents.
そこで、本発明者らは先に、上記の欠点を克服すべく研
究を重ねた結果、α−フェニルエチルアルコール誘導体
をロジウム触媒とヨウ素化合物の存在下に一酸化炭素と
反応させることにより、α−フェニルプロピオン酸誘導
体を好収率で得る工業的に有利な方法を見出し、特許出
願した（昭和６１年４月１５日提出の特許願（１））。Therefore, as a result of repeated research to overcome the above-mentioned drawbacks, the present inventors discovered that α-phenylethyl alcohol derivatives were reacted with carbon monoxide in the presence of a rhodium catalyst and an iodine compound. They discovered an industrially advantageous method for obtaining phenylpropionic acid derivatives in good yields and filed a patent application (patent application (1) filed on April 15, 1988).
本発明者らは上記発明にいたる研究に際して、反応に使
用する溶媒を変えることにより、α−フェニルプロピオ
ン酸誘導体の収率が極めて大幅に変化することに着目し
、より一層の収率向上を目指し、各種反応溶媒の検討を
鋭意重ねた結果、意外にも、炭化水素と含酸素有機化合
物とを混合した溶媒を反応に使用することにより、それ
ぞれを単独で溶媒として用いた場合に比し、大幅にα−
フェニルプロピオン酸誘導体の収率が向上することを見
出し、本発明の完成に至ったものである。During the research that led to the above invention, the present inventors focused on the fact that the yield of α-phenylpropionic acid derivatives changes significantly by changing the solvent used in the reaction, and aimed to further improve the yield. As a result of intensive studies on various reaction solvents, surprisingly, by using a mixed solvent of hydrocarbon and oxygen-containing organic compound in the reaction, the reaction rate was significantly greater than when each solvent was used alone. α−
It was discovered that the yield of phenylpropionic acid derivatives was improved, and the present invention was completed.
即ち、本発明は、
（式中、Ｒは水素、アルキル基、アルケニル基、又はア
リール基を表す）
で示されるα−フェニルエチルアルコール誘導体を、炭
化水素と含酸素有機化合物とを混合した溶媒中において
、触媒の存在下に一酸化炭素と反応させることを特徴と
する一般式
で示されるα−フェニルプロピオン酸誘導体の製造法に
係わるものである。That is, the present invention provides an α-phenylethyl alcohol derivative represented by (wherein R represents hydrogen, an alkyl group, an alkenyl group, or an aryl group) in a solvent containing a mixture of a hydrocarbon and an oxygen-containing organic compound. The present invention relates to a method for producing an α-phenylpropionic acid derivative represented by the general formula, which comprises reacting with carbon monoxide in the presence of a catalyst.
以下、本発明を具体的に説明する。The present invention will be specifically explained below.
（１１原料アルコール
■
で示される原料となるα−フェニルエチルアルコール誘
導体において、置換基Ｒは水素、アルキル基、アルケニ
ル基、又はアリール基を表す、アルキル基、アルケニル
基としては、鎖状、分枝状あるいは環状のもの、例えば
メチル基、エチル基、プロピル基、イソブチル基、イソ
プレニル基、シクロヘキシル基等が挙げられる。アリー
ル基としては、例えばフェニル基、トリル基、キシリル
基、ナフチル基等が挙げられる。(11 Raw material alcohol ■ In the α-phenylethyl alcohol derivative that is the raw material, the substituent R represents hydrogen, an alkyl group, an alkenyl group, or an aryl group. Examples of aryl groups include phenyl, tolyl, xylyl, naphthyl, etc. .
（２）溶媒
本発明は、反応溶媒として炭化水素と含酸素有機化合物
との混合物を用いることにその特徴がある。炭化水素と
しては、反応条件下で液体として存在し得るものであれ
ばいずれも使用可能で、例えば、ペンタン、ヘキサン、
シクロヘキサン等の脂肪族炭化水素類、ベンゼン、トル
エン、キシレン等の芳香族炭化水素類、及びそれらの混
合物が通常用いられる。(2) Solvent The present invention is characterized by using a mixture of a hydrocarbon and an oxygen-containing organic compound as a reaction solvent. Any hydrocarbon that can exist as a liquid under the reaction conditions can be used, such as pentane, hexane,
Aliphatic hydrocarbons such as cyclohexane, aromatic hydrocarbons such as benzene, toluene, xylene, and mixtures thereof are commonly used.
含酸素有機化合物としては、例えば、酢酸、プロピオン
酸、安息香酸等の有機カルボン酸類、アセトン、メチル
エチルケトン等のケトン類、ジオキサン、テトラハイド
ロフラン、ジエチルエーテル等のエーテル類及びそれら
の混合物が好ましく用いられる。As the oxygen-containing organic compound, for example, organic carboxylic acids such as acetic acid, propionic acid, and benzoic acid, ketones such as acetone and methyl ethyl ketone, ethers such as dioxane, tetrahydrofuran, and diethyl ether, and mixtures thereof are preferably used. .
炭化水素と含酸素有機化合物との最適な混合比は、用い
られる両者の化合物の種類により大きく異なるが、ヘキ
サンと酢酸との混合物での例を挙げれば、酢酸／ヘキサ
ン容量比で２／９８〜３０／７０程度が好ましい結果を
与える。The optimal mixing ratio of hydrocarbon and oxygen-containing organic compound varies greatly depending on the types of both compounds used, but for example, in the case of a mixture of hexane and acetic acid, the acetic acid/hexane volume ratio is 2/98 to 2/98. A ratio of about 30/70 gives preferable results.
また、上記混合溶媒中における、原料アルコールの濃度
としては、通常１〜５０重量％程度が好ましい。Further, the concentration of the raw material alcohol in the mixed solvent is usually preferably about 1 to 50% by weight.
（３）触媒
本発明は、触媒として遷移金属化合物及び必要に応じて
助触媒の存在下で実施される。(3) Catalyst The present invention is carried out in the presence of a transition metal compound as a catalyst and, if necessary, a co-catalyst.
遷移金属化合物中の金属としては、ロジウム、パラジウ
ム、コバルト、ニッケル等が挙げられ、助触媒としては
、ハロゲン族原子、三価の燐化合物等が挙げられる。就
中、本発明においては、遷移金属化合物としてロジウム
化合物、助触媒としてヨウ素の組み合わせが好ましい結
果を与える。具体的には、ロジウム化合物としては、ハ
ロゲン化ロジウム、ロジウムカルボニル、酢酸ロジウム
等が、ヨウ素助触媒としては、Ｉｚ、旧、ヨウ化アルキ
ル等のヨウ素化合物が一般的に用いられる。またロジウ
ム化合物としてヨウ化ロジウムを用いる場合は、助触媒
としてヨウ素化合物を必ずしも追加する必要はない。Examples of the metal in the transition metal compound include rhodium, palladium, cobalt, nickel, etc., and examples of the promoter include halogen group atoms, trivalent phosphorus compounds, and the like. In particular, in the present invention, a combination of a rhodium compound as the transition metal compound and iodine as the co-catalyst gives preferable results. Specifically, as the rhodium compound, rhodium halide, rhodium carbonyl, rhodium acetate, etc. are generally used, and as the iodine promoter, iodine compounds such as Iz, former, alkyl iodide, etc. are generally used. Further, when rhodium iodide is used as the rhodium compound, it is not necessarily necessary to add an iodine compound as a promoter.
（４）−酸化炭素
一酸化炭素は、純粋なもの、またはこれに窒素等の不活
性ガス、あるいは水素を含むものが使用可能である。反
応圧力は、常圧でも高圧でも反応は進行するが、反応速
度及び経済的な面からは、常圧〜１００ｋｇ／ｃａ＋”
が好ましい。また水素を含む場合、その分圧が常圧〜５
ｋｇ／ｃ＋ａ！程度であれば、遷移金属化合物の溶解を
助ける意味でむしろ好ましいが、それ以上の高圧の場合
、水素化副生物を増加させ不利である。(4) - Carbon oxide Carbon monoxide may be pure or may contain an inert gas such as nitrogen, or hydrogen. The reaction proceeds at both normal pressure and high pressure, but from the viewpoint of reaction rate and economy, the reaction pressure is between normal pressure and 100 kg/ca+.
is preferred. In addition, when hydrogen is included, its partial pressure is between normal pressure and 5.
kg/c+a! If the pressure is higher than that, it is preferable in the sense that it helps dissolve the transition metal compound, but if the pressure is higher than that, hydrogenation by-products will increase, which is disadvantageous.
（５）反応温度
反応温度は通常３０℃〜１３０℃であるが、経済的な面
及び副反応抑制の面から６０℃〜１００℃が好ましい。(5) Reaction temperature The reaction temperature is usually 30°C to 130°C, but preferably 60°C to 100°C from the economical and side reaction viewpoints.
以下、実施例を挙げて本発明を更に具体的に説明するが
、本発明はこれらの実施例に限定されるものではない。EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
実施例１
ハステロイ製、容量３００−のオートクレーブにα−（
４−イソブチルフェニル）エチルアルコール９．８ｇ
（５５，１ｍｍｏｌ） 、ヨウ化ロジウム１．５ｇ （
３，１０ｍｍｏｌ） 、及び溶媒として酢酸５ｍ７、ヘ
キサン９５ｍ１を入れ、水素圧力１ａｔｍ、−酸化炭素
圧力６ｋｇ／ｃａｂ” 、反応温度８５℃で３時間攪拌
しながら反応させた。冷却後、内容物を取り出し溶媒を
減圧留去した。残渣をヘンイソ５０＠７に溶解し、２Ｎ
−ＮａＯ）１水溶液１００ ｍ７を加え、酸成分を水層
に抽出した。抽出液に塩酸を加え遊離した酸をエーテル
に抽出した。エーテルを留去して得た粗結晶をｎ−ヘキ
サン中で再結晶させα−（４−イソブチルフェニル）プ
ロピオン酸の白色結晶６．９ ｇ （３３，５ｍｍｏｌ
）を得た（収率６０．８％）。Example 1 α-(
9.8 g of 4-isobutylphenyl)ethyl alcohol
(55.1 mmol), rhodium iodide 1.5 g (
3,10 mmol), and 5 m7 of acetic acid and 95 ml of hexane as solvents, and the mixture was reacted with stirring at a hydrogen pressure of 1 atm, a carbon oxide pressure of 6 kg/cab, and a reaction temperature of 85°C for 3 hours. After cooling, the contents were taken out. The solvent was distilled off under reduced pressure.The residue was dissolved in Heniso 50@7 and diluted with 2N
-NaO)1 aqueous solution (100 m7) was added to extract the acid component into the aqueous layer. Hydrochloric acid was added to the extract, and the liberated acid was extracted into ether. The crude crystals obtained by distilling off the ether were recrystallized in n-hexane to give 6.9 g (33.5 mmol) of white crystals of α-(4-isobutylphenyl)propionic acid.
) was obtained (yield 60.8%).
実施例２〜３、比較例１〜４
表１に示す溶媒、原料アルコール、触媒を用い、表１に
示す条件で実施例１に準じて反応を行った。その結果を
表１に示した。Examples 2 to 3, Comparative Examples 1 to 4 A reaction was carried out according to Example 1 under the conditions shown in Table 1 using the solvent, raw material alcohol, and catalyst shown in Table 1. The results are shown in Table 1.
上記実施例からも明らかなように、本発明の製造法によ
ると、大幅にα−フェニルプロピオン酸誘導体の収率を
向上させることができる。As is clear from the above examples, according to the production method of the present invention, the yield of α-phenylpropionic acid derivatives can be significantly improved.
Claims (1)
リール基を表す） で示されるα−フェニルエチルアルコール誘導体を、炭
化水素と含酸素有機化合物とを混合した溶媒中において
、触媒の存在下に一酸化炭素と反応させることを特徴と
する一般式 ▲数式、化学式、表等があります▼（式中Ｒは前記と同
意義） で示されるα−フェニルプロピオン酸誘導体の製造法。[Claims] An α-phenylethyl alcohol derivative represented by the general formula ▲ includes numerical formulas, chemical formulas, tables, etc. ▼ (in the formula, R represents hydrogen, an alkyl group, an alkenyl group, or an aryl group), There are general formulas that are characterized by reacting with carbon monoxide in the presence of a catalyst in a mixed solvent of hydrogen and an oxygen-containing organic compound. There are mathematical formulas, chemical formulas, tables, etc. (in the formula, R is the same as above) Significance) A method for producing an α-phenylpropionic acid derivative represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61106403A JPH0625088B2 (en) | 1986-05-09 | 1986-05-09 | Process for producing α-phenylpropionic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61106403A JPH0625088B2 (en) | 1986-05-09 | 1986-05-09 | Process for producing α-phenylpropionic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62263140A true JPS62263140A (en) | 1987-11-16 |
| JPH0625088B2 JPH0625088B2 (en) | 1994-04-06 |
Family
ID=14432717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61106403A Expired - Lifetime JPH0625088B2 (en) | 1986-05-09 | 1986-05-09 | Process for producing α-phenylpropionic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0625088B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0285229A (en) * | 1988-09-22 | 1990-03-26 | Mitsubishi Gas Chem Co Inc | Production of alpha-(4-isobutylphenyl) propionic acid |
| US5166418A (en) * | 1990-06-04 | 1992-11-24 | Hoechst Celanese Corporation | Method for producing ibuprofen |
| US5271811A (en) * | 1988-01-29 | 1993-12-21 | Hoechst Celanese Corporation | Process for purifying 2-(4-isobutylphenyl)-propionic acid by vacuum distillation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5527147A (en) * | 1978-08-16 | 1980-02-27 | Mitsubishi Petrochem Co Ltd | Preparation of carboxylic acid having aryl substituent |
-
1986
- 1986-05-09 JP JP61106403A patent/JPH0625088B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5527147A (en) * | 1978-08-16 | 1980-02-27 | Mitsubishi Petrochem Co Ltd | Preparation of carboxylic acid having aryl substituent |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5271811A (en) * | 1988-01-29 | 1993-12-21 | Hoechst Celanese Corporation | Process for purifying 2-(4-isobutylphenyl)-propionic acid by vacuum distillation |
| JPH0285229A (en) * | 1988-09-22 | 1990-03-26 | Mitsubishi Gas Chem Co Inc | Production of alpha-(4-isobutylphenyl) propionic acid |
| US5166418A (en) * | 1990-06-04 | 1992-11-24 | Hoechst Celanese Corporation | Method for producing ibuprofen |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0625088B2 (en) | 1994-04-06 |
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