JPH0248544A - Production of alpha-phenylpropionic acid derivative - Google Patents
Production of alpha-phenylpropionic acid derivativeInfo
- Publication number
- JPH0248544A JPH0248544A JP63198489A JP19848988A JPH0248544A JP H0248544 A JPH0248544 A JP H0248544A JP 63198489 A JP63198489 A JP 63198489A JP 19848988 A JP19848988 A JP 19848988A JP H0248544 A JPH0248544 A JP H0248544A
- Authority
- JP
- Japan
- Prior art keywords
- alpha
- phenylpropionic acid
- acid derivative
- reaction
- solvent
- 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
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical class CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 27
- 238000006243 chemical reaction Methods 0.000 abstract description 25
- 239000002904 solvent Substances 0.000 abstract description 12
- 229930195733 hydrocarbon Natural products 0.000 abstract description 7
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 6
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- KXAHUXSHRWNTOD-UHFFFAOYSA-K rhodium(3+);triiodide Chemical compound [Rh+3].[I-].[I-].[I-] KXAHUXSHRWNTOD-UHFFFAOYSA-K 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 206010037660 Pyrexia Diseases 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001741 anti-phlogistic 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
- 239000002253 acid Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000003623 transition metal compounds Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 150000002497 iodine compounds Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003284 rhodium compounds Chemical class 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-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
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 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
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 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
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 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
- 239000000047 product Substances 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- -1 rhodium halide Chemical class 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
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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−７エニルプロピオン酸訪導体の工業的製
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 an α-7 enylpropionic acid visiting conductor.
α−フェニルゾ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-Phenylzolopionic acid derivatives have pharmacological effects such as analgesia, anti-inflammatory, and antipyretic properties, and are useful as pharmaceuticals.
〔従来の技術及び発明が解決しようとする課題〕α−フ
エエルグ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。[Prior art and problems to be solved by the invention] Many synthetic routes have been proposed in recent years for the production of α-pheergropionic acid derivatives, but all of them require long reaction steps, are expensive, and In addition, the process was not industrially satisfactory due to the use of toxic reagents.
そこで、本出願人は先に、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
ロノ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−フェニルゾロピオン酸誘導体
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。（特開昭６２−２４２６４２）
本出願人は上記発明にいたる研究に際して、反応溶媒と
して炭化水素と含酸素化合物との混合物が有効であると
して特許出願した。（特開昭６２−２６３１４０）Ｌか
し、まだ十分満足できる収率を達成することができなか
った。Therefore, as a result of repeated research in order to overcome the above-mentioned drawbacks, the applicant of the present invention discovered that α-phenylethyl alcohol derivatives were reacted with carbon monoxide in the presence of a ronium catalyst and an iodine compound. He discovered an industrially advantageous method for obtaining zolopionic acid derivatives in good yields and filed a patent application. (Japanese Unexamined Patent Publication No. 62-242642) During the research leading to the above invention, the present applicant filed a patent application claiming that a mixture of a hydrocarbon and an oxygen-containing compound is effective as a reaction solvent. (JP-A-62-263140) However, a sufficiently satisfactory yield could not yet be achieved.
本発明者は前記の反応溶媒について更に検討し次結果、
意外にも、炭化水素とα−フェニル！ロピオン酸誘導体
ｋｉ媒として反応に使用することにより、炭化水素にα
−フェニルプロピオン酸誘導体以外の含酸素化合物とを
混合した溶媒より太幅に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。The inventor further studied the above reaction solvent and found the following results:
Surprisingly, hydrocarbons and α-phenyl! By using ropionic acid derivatives as ki medium in the reaction, α
It has been found that the yield of α-phenylpropionic acid derivatives is significantly improved compared to a solvent mixed with an oxygen-containing compound other than -phenylpropionic acid derivatives, and the present invention has been 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α−フェニルプロピオン酸誘導体とを混合した
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形式で示されるα−７エニルゾロ
ビオン峻訪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) mixed with a hydrocarbon and an α-phenylpropionic acid derivative. The present invention relates to a method for producing an α-7 enylzolobion radical conductor, which is characterized in that it is reacted with carbon monoxide in a solvent 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 explained in detail below.
（１）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、グロビル基、インブチル基、イン
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。(1) In the α-phenylethyl alcohol derivative serving as a raw material represented by raw material alcohol, the substituent R represents hydrogen, an alkyl group, an alkenyl group, or an aryl group. Examples of the alkyl group and alkenyl group include chain, branched, or cyclic groups, such as methyl group, ethyl group, globyl group, inbutyl group, imprenyl group, and cyclohexyl group. Examples of the aryl group include phenyl group, tolyl group, xylyl group, and naphthyl group.
（２） 溶 媒
本発明は、反応溶媒として炭化水素とα−フェニルプロ
ピオン酸誘導体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、被ンタ
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。炭化水素とα−
フェニルプロピオン酸誘導体との最適な混合比は、用い
られる両者の化合物の拙類により大きく異なるが、ヘキ
サンとα−フェニルプロピオン酸誘導体との混合物での
例を挙げれば、α−７エニルゾロピオン酸誘導体／ヘキ
サンの重量比で１／３ｏ〜１／８で好ましくは、１７１
０〜ｌ／１６程度が良い結果を与える。(2) Solvent The present invention is characterized by using a mixture of a hydrocarbon and an α-phenylpropionic acid derivative as a reaction solvent. Any hydrocarbon can be used as long as it can exist as a liquid under the reaction conditions; for example, aliphatic hydrocarbons such as ethane, hexane, and cyclohexane;
Aromatic hydrocarbons such as benzene, toluene, xylene,
and mixtures thereof are commonly used. Hydrocarbons and α−
The optimal mixing ratio with the phenylpropionic acid derivative varies greatly depending on the type of both compounds used, but to give an example of a mixture of hexane and α-phenylpropionic acid derivative, α-7enylzolopionic acid derivative/α-7enylzolopionic acid derivative/ The weight ratio of hexane is 1/3 to 1/8, preferably 171
A value of about 0 to 1/16 gives good results.
溶媒として用いるα−フェニルプロピオン酸誘導体と製
品として得るα−フェニルプロピオン酸誘導体は違うも
のでも良いが、反応後の精製等を考えると同じ物が良い
。Although the α-phenylpropionic acid derivative used as a solvent and the α-phenylpropionic acid derivative obtained as a product may be different, they are preferably the same in consideration of purification after the reaction.
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１〜５０Ｔｉｉ％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%.
（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。遷移金属化合物中の金属
としては、ロノウム、ノ！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、ハロゲノ族原子、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、Ｉａ ｅ ＨＩ ｅ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。(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. Metals in transition metal compounds include ronium, no! Examples include radium, cobalt, nickel, etc., and examples of cocatalysts include halogeno group atoms, trivalent phosphorus compounds, etc. 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 Ia e HI e alkyl iodide 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
性がス、あるいは水素を含むものが使用可能である０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〜１００ Ｋｇ／ｃｍ２
が好ましい。また水素を含む場合、その分圧が常圧〜５
Ｋｇ／α２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 can be pure, or it can contain an inert gas such as nitrogen, or hydrogen.The reaction proceeds at zero reaction pressure, whether it is normal pressure or high pressure. However, from the viewpoint of reaction rate and economy, normal pressure to 100 Kg/cm2
is preferred. In addition, when hydrogen is included, its partial pressure is between normal pressure and 5.
A pressure of about Kg/α2 is rather preferable in the sense that it helps dissolve the transition metal compound, but higher pressures are disadvantageous because they increase hydrogenation by-products.
（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ｔ３Ｊのオートクレーブにα−（４−
インブチルフェニル〕エチルアルコール１６０５’ （
０，８９９ｍｏｔ） Ｅつ化ロジウム１５．０？ （０
，０３１ｍｏｔ）、及び溶媒としてα−（４一イソブチ
ルフエニル〕グロピオンｗｓｏｙ、ヘキサン６３７．５
Ｐを入れ、−酸化炭素圧力１６ Ｋｙ／暦、反応温度７
５℃で反応させたところ、反応開始後１８時間でガス吸
収が止まり反応が終了した。冷却後、反応液を取り出し
、ガスクロマトグラムで分析した。その結果α−（４−
インブチルフェニル）ｆロビオン酸１５７．４Ｐを得た
。収率８５チ比較例１
実施例１で溶媒をヘキサン７１５１酢酸６０Ｐの混合溶
媒を用いて反応した場合収率は、７５％であった。Example 1 α-(4-
imbutylphenyl]ethyl alcohol 1605' (
0,899mot) Rhodium chloride 15.0? (0
, 031mot), and α-(4-isobutylphenyl)gropion wsoy, hexane 637.5 as a solvent.
Add P, -carbon oxide pressure 16 Ky/calendar, reaction temperature 7
When the reaction was carried out at 5°C, gas absorption stopped and the reaction was completed 18 hours after the start of the reaction. After cooling, the reaction solution was taken out and analyzed by gas chromatography. As a result α−(4−
(butylphenyl) f-robionic acid 157.4P was obtained. Yield: 85% Comparative Example 1 When the reaction was carried out in Example 1 using a mixed solvent of 7151 hexane and 60P acetic acid, the yield was 75%.
実施例２
実施例１と同様な方法で反応温度を８５℃にして反応さ
せたところ、反応開始後１３時間でガス吸収が止まり反
応が終了した。冷却後、反応液を取り出し、ガスクロマ
トグラムで分析した。その結果α−（４−インブチルフ
ェニル〕グロピオンｒｆ１１４２．６５”ｅ得た。収率
７７％比較例２
実施例２の反応を溶媒をヘキサン７１５７、酢酸６０５
’の混合溶媒を用いて反応した場合、収率は７０チであ
った。Example 2 When the reaction was carried out in the same manner as in Example 1 at a reaction temperature of 85°C, gas absorption stopped and the reaction was completed 13 hours after the start of the reaction. After cooling, the reaction solution was taken out and analyzed by gas chromatography. As a result, α-(4-inbutylphenyl)gropion rf1142.65"e was obtained. Yield 77% Comparative Example 2 The reaction of Example 2 was carried out using hexane 7157 and acetic acid 605 as the solvent.
When the reaction was carried out using a mixed solvent of ', the yield was 70%.
比較例３
実施例１の反応を溶媒をヘキサン７７５１の単独溶媒で
反応した場合、収率は、５２％であった。Comparative Example 3 When the reaction of Example 1 was carried out using hexane 7751 as the sole solvent, the yield was 52%.
この結果より反応途中で生成してくるα−（４−インプ
チルフエニル）−グロピオン酸では、収率向上に有効で
ないことがわかった。From this result, it was found that α-(4-impltylphenyl)-gropionic acid produced during the reaction is not effective in improving the yield.
上記実施例からも明らかなように、本発明の製造法によ
ると特定の溶媒を用いるだけで、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 simply by using a specific solvent.
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α−フェニルプロピオン酸誘導体とを混合した
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 α-phenylpropionic acid derivative. There are mathematical formulas, chemical formulas, tables, etc. (in the formula, R is the A method for producing an α-phenylpropionic acid derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63198489A JPH0248544A (en) | 1988-08-09 | 1988-08-09 | Production of alpha-phenylpropionic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63198489A JPH0248544A (en) | 1988-08-09 | 1988-08-09 | Production of alpha-phenylpropionic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0248544A true JPH0248544A (en) | 1990-02-19 |
Family
ID=16391968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63198489A Pending JPH0248544A (en) | 1988-08-09 | 1988-08-09 | Production of alpha-phenylpropionic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0248544A (en) |
Cited By (1)
| 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 |
-
1988
- 1988-08-09 JP JP63198489A patent/JPH0248544A/en active Pending
Cited By (1)
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS60500282A (en) | Leaching-resistant catalyst useful for dimerization of acrylic compounds | |
| JPH0248544A (en) | Production of alpha-phenylpropionic acid derivative | |
| JPS63159341A (en) | Production of alpha-phenylpropionic acid derivative | |
| JPS62263140A (en) | Production of alpha-phenylpropionic acid derivative | |
| JPS6035347B2 (en) | Synthesis method of α-tocopherol | |
| Fan et al. | Rhodium catalyzed asymmetric Pauson-Khand reaction using SDP ligands | |
| JPH0557250B2 (en) | ||
| JPH01233255A (en) | Cyclopentenone derivative and production thereof | |
| JP3691235B2 (en) | Process for producing optically active piperidines | |
| JPS6038343A (en) | Production of phenylacetic acid derivative | |
| JPS60158124A (en) | Manufacture of 1,4-butanediol | |
| JPS6137753A (en) | Method of oxidizing cinnamic aldehyde | |
| Klingler et al. | Catalytic methanol synthesis from carbon monoxide and water | |
| JPS5944303B2 (en) | Production method of α-ketoacids | |
| JPH0285229A (en) | Production of alpha-(4-isobutylphenyl) propionic acid | |
| JP3292559B2 (en) | Method for producing catechol derivative | |
| JPS6157532A (en) | Manufacture of phenylacetic acid and derivatives of same by catalytic rearrangement of benzyl formate and derivatives ofsame | |
| JPS62242641A (en) | Production of alpha-phenylpropionic acid derivative | |
| JPS59157053A (en) | Manufacture of ester | |
| JPS5944304B2 (en) | Method for producing α-ketoamides | |
| JPS6314698B2 (en) | ||
| JPS588382B2 (en) | Amino Sanno Seizouhou | |
| JPH0386840A (en) | Production of alpha,beta-unsaturated carbonyl compound | |
| JPH09309887A (en) | Samarium complex | |
| Kubota et al. | CH bond cleavage in alkenyl carboxylates promoted by methylcopper complexes and formation of six-membered acetoxyvinylcopper chelates |