JP2009155273A - Method for producing cyclic ketone - Google Patents
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本発明は、芳香環置換フェニルアルカン酸を、触媒存在下で分子内環化させて得られる環状ケトンの効率的な製造方法に関するものである。 The present invention relates to an efficient method for producing a cyclic ketone obtained by intramolecular cyclization of an aromatic ring-substituted phenylalkanoic acid in the presence of a catalyst.
テトラロン、インダノン、ベンゾスベロン等の環状ケトン（芳香環縮合シクロアルケノン）は、医・農薬等の生理活性物質やその合成中間体として有用である。
それらの製造法として、芳香環置換アルカン酸を、酸触媒存在下で、フリーデル・クラフツ型反応により環化させる方法が知られているが、従来の製造法では、反応を進行させるために、多量の酸触媒の使用や高温での長時間の加熱等が必要であり（たとえば、非特許文献１〜２、特許文献１）、工業的に有利な方法とはいえなかった。
As a production method thereof, a method of cyclizing an aromatic ring-substituted alkanoic acid by Friedel-Crafts type reaction in the presence of an acid catalyst is known, but in the conventional production method, in order to proceed the reaction, The use of a large amount of an acid catalyst and long-time heating at a high temperature are necessary (for example, Non-Patent Documents 1 and 2 and Patent Document 1), and it was not an industrially advantageous method.
本発明は、以上のような事情に鑑みてなされたものであって、芳香環置換アルカン酸から環状ケトンを、多量の酸性廃棄物を出すことなく短時間で効率的に製造することを目的とするものである。 The present invention has been made in view of the circumstances as described above, and an object thereof is to efficiently produce a cyclic ketone from an aromatic ring-substituted alkanoic acid in a short time without producing a large amount of acidic waste. To do.
本発明者らは、上記課題を解決すべく鋭意研究を重ねた結果、芳香環置換アルカン酸の分子内環化反応が、マイクロ波照射により著しく加速されることを見いだし、本発明を完成させるに至った。
すなわち、この出願は以下の発明を提供するものである。
〈１〉下記の一般式（Ｉ）
で表される芳香環置換アルカン酸を、触媒の存在下で、マイクロ波を照射して反応させることを特徴とする、下記の一般式（ＩＩ）
で表される環状ケトンの製造方法。
〈２〉触媒が酸触媒であることを特徴とする〈１〉に記載の製造方法。
〈３〉酸触媒が、固体酸であることを特徴とする〈２〉に記載の製造方法。
〈４〉固体酸が、ゼオライト、モンモリロナイト、シリカ及び酸性ポリマーから選ばれる少なくとも一種であることを特徴とする〈３〉に記載の製造方法。
As a result of intensive studies to solve the above problems, the present inventors have found that the intramolecular cyclization reaction of an aromatic ring-substituted alkanoic acid is remarkably accelerated by microwave irradiation, thereby completing the present invention. It came.
That is, this application provides the following inventions.
<1> The following general formula (I)
Wherein the aromatic ring-substituted alkanoic acid is reacted by irradiation with microwaves in the presence of a catalyst.
The manufacturing method of cyclic ketone represented by these.
<2> The production method according to <1>, wherein the catalyst is an acid catalyst.
<3> The production method according to <2>, wherein the acid catalyst is a solid acid.
<4> The production method according to <3>, wherein the solid acid is at least one selected from zeolite, montmorillonite, silica, and an acidic polymer.
本発明の製法方法により、従来の方法に比べ短時間で効率的に環状ケトン（芳香環縮合シクロアルケノン）を得ることができる。 By the production method of the present invention, a cyclic ketone (aromatic ring-fused cycloalkenone) can be efficiently obtained in a shorter time than the conventional method.
以下、本発明について詳細に説明する。
本発明の製造方法は、芳香環置換アルカン酸を、触媒の存在下、マイクロ波を照射して反応させることを特徴とする。
本発明において使用される芳香環置換アルカン酸は、下記の一般式（Ｉ）
そのような環Ａの種類としては、ベンゼン環、ナフタレン環、フラン環、チオフェン環等が挙げられ、それらの環を有する芳香環置換アルカン酸の具体例としては、３−フェニルプロピオン酸、４−フェニル酪酸、４−（４−メトキシフェニル）酪酸、４−（４−トリル）酪酸、４−（４−フルオロフェニル）酪酸、４−（４−クロロフェニル）酪酸、４−（４−ニトロフェニル）酪酸、４−（２，５−ジメトキシフェニル）酪酸、５−フェニル吉草酸、６−フェニルヘキサン酸、７−フェニルヘプタン酸、８−フェニルオクタン酸、９−フェニルノナン酸、９−フェニルデカン酸、４−（２−フリル）ブタン酸、４−（２−チエニル）ブタン酸、４−（２−セレノフェニル）ブタン酸、３−（２−フリル）プロパン酸、３−（２−チエニル）プロパン酸等を挙げることができる。
Hereinafter, the present invention will be described in detail.
The production method of the present invention is characterized by reacting an aromatic ring-substituted alkanoic acid by irradiation with microwaves in the presence of a catalyst.
The aromatic ring-substituted alkanoic acid used in the present invention has the following general formula (I)
Examples of such ring A include a benzene ring, a naphthalene ring, a furan ring, a thiophene ring, and the like. Specific examples of the aromatic ring-substituted alkanoic acid having such a ring include 3-phenylpropionic acid, 4-phenyl Phenylbutyric acid, 4- (4-methoxyphenyl) butyric acid, 4- (4-tolyl) butyric acid, 4- (4-fluorophenyl) butyric acid, 4- (4-chlorophenyl) butyric acid, 4- (4-nitrophenyl) butyric acid 4- (2,5-dimethoxyphenyl) butyric acid, 5-phenylvaleric acid, 6-phenylhexanoic acid, 7-phenylheptanoic acid, 8-phenyloctanoic acid, 9-phenylnonanoic acid, 9-phenyldecanoic acid, 4 -(2-furyl) butanoic acid, 4- (2-thienyl) butanoic acid, 4- (2-selenophenyl) butanoic acid, 3- (2-furyl) propanoic acid, 3- (2-thienyl) And the like can be given propanoic acid.
一方、本発明で製造される環状ケトンは、下記の一般式（ＩＩ）
それらの具体例としては、ベンゾシクロブテノン、ベンゾシクロペンテノン（１−インダノン）、ベンゾシクロヘキセノン（１−テトラロン）、７−メチル−１−テトラロン、７−メトキシ−１−テトラロン、７−フルオロ−１−テトラロン、７−ニトロ−１−テトラロン、５，８−ジメトキシ−１−テトラロン、ベンゾシクロヘプテノン（１−ベンゾスベロン）、ベンゾシクロオクテノン、ベンゾシクロノネノン、ベンゾシクロデセノン、ベンゾシクロドデセノン、４−オキソ−４，５，６，７−テトラヒドロオキサナフテン、４−オキソ−４，５，６，７−テトラヒドロチアナフテン、４−オキソ−４，５，６，７−テトラヒドロセレナナフテン等を挙げることができる。
On the other hand, the cyclic ketone produced in the present invention has the following general formula (II):
Specific examples thereof include benzocyclobutenone, benzocyclopentenone (1-indanone), benzocyclohexenone (1-tetralone), 7-methyl-1-tetralone, 7-methoxy-1-tetralone, 7-fluoro. -1-tetralone, 7-nitro-1-tetralone, 5,8-dimethoxy-1-tetralone, benzocycloheptenone (1-benzosuberone), benzocyclooctenone, benzocyclononenone, benzocyclodecenone, benzocyclo Dodecenone, 4-oxo-4,5,6,7-tetrahydrooxanaphthene, 4-oxo-4,5,6,7-tetrahydrothianaphthene, 4-oxo-4,5,6,7-tetrahydroselena Naphthenes can be mentioned.
本発明では、フリーデル・クラフツ型の求電子置換反応で使われる従来公知の各種の触媒を用いることができる。それらの具体例としては、金属塩、金属酸化物等の無機物、有機物等、各種酸性化合物が挙げられ、無機物をより具体的に示せば、金属塩（アルミニウム、鉄等の塩化物、臭化物等）や、プロトン性水素原子あるいは金属カチオン（アルミニウム、チタン、ガリウム等）を有するゼオライト、モンモリロナイト、シリカ、ポリリン酸等の無機系固体酸が挙げられ、また有機物をより具体的に示せば、スルホン酸基を有するナフィオン等の酸性ポリマーや他の有機系固体酸が挙げられる。この中のゼオライトの種類としては、Ｙ型、Ｂｅｔａ型、ＺＳＭ−５型、Ｍｏｒｄｅｎｉｔｅ型、ＳＡＰＯ型等の基本骨格を有する各種のゼオライトを使用できる。また、シリカ等にナフィオン等の有機系酸性化合物を担持した触媒を用いることもできる。触媒の量は、所望する反応速度等に応じて任意に決めることができるが、原料に対する重量比として、通常０．０００１〜２００であり、好ましくは０．００２〜１５０、より好ましくは０．００５〜１００である。 In the present invention, various conventionally known catalysts used in Friedel-Crafts type electrophilic substitution reactions can be used. Specific examples thereof include various acidic compounds such as metal salts, inorganic substances such as metal oxides, and organic substances. If inorganic substances are shown more specifically, metal salts (chlorides such as aluminum and iron, bromides, etc.) And inorganic solid acids such as zeolites having protonic hydrogen atoms or metal cations (aluminum, titanium, gallium, etc.), montmorillonite, silica, polyphosphoric acid, etc., and more specifically showing organic substances, sulfonic acid groups And acidic polymers such as Nafion and other organic solid acids. Among these, various types of zeolite having a basic skeleton such as Y-type, Beta-type, ZSM-5-type, Mordenite-type, and SAPO-type can be used. A catalyst in which an organic acidic compound such as Nafion is supported on silica or the like can also be used. The amount of the catalyst can be arbitrarily determined according to the desired reaction rate and the like, but is usually 0.0001 to 200, preferably 0.002 to 150, more preferably 0.005 as a weight ratio to the raw material. ~ 100.
反応の温度は、−２０℃以上、好ましくは０〜３００℃、より好ましくは、４０〜２９０℃であり、反応時間は反応温度にもよるが、０．５〜１２０分、好ましくは０．５〜１００分、より好ましくは０．５〜８０分程度である。 The temperature of the reaction is −20 ° C. or higher, preferably 0 to 300 ° C., more preferably 40 to 290 ° C. The reaction time depends on the reaction temperature, but is 0.5 to 120 minutes, preferably 0.5 -100 minutes, more preferably about 0.5-80 minutes.
また、反応は、溶媒の有無にかかわらず実施できるが、溶媒を用いる場合には、デカリン、デカン等の炭化水素、クロロベンゼン、１，２−又は１，３−ジクロロベンゼン、１，２，４−トリクロロベンゼン等のハロゲン化炭化水素、ジブチルエーテル等のエーテル等、原料と反応するものを除いた各種の溶媒が使用可能で、２種以上混合して用いることもできる。 The reaction can be carried out with or without a solvent. When a solvent is used, hydrocarbons such as decalin and decane, chlorobenzene, 1,2- or 1,3-dichlorobenzene, 1,2,4- Various solvents excluding those that react with the raw material, such as halogenated hydrocarbons such as trichlorobenzene and ethers such as dibutyl ether, can be used, and two or more kinds can be used in combination.
本発明において照射するマイクロ波の出力や周波数、照射方法は、特に限定されるものではなく、反応温度が所定の範囲に保持できるように制御すればよい。マイクロ波の周波数は、通常、０．３ＧＨｚ〜３０ＧＨｚである。０．３ＧＨｚ未満又は３０ＧＨｚを超える周波数範囲では、環化反応が不十分となり環状ケトンの形成促進効果が不十分となる。
本発明の反応におけるマイクロ波の照射では、接触式または非接触式の温度センサーを備えた各種の市販装置等を使用できる。さらに、マイクロ波照射の出力、キャビティの種類（マルチモード、シングルモード）、照射の形態（連続的、断続的）等は、反応のスケールや種類等に応じて任意に決めることができる。
マイクロ波発振器としては、マグネトロン等のマイクロ波発振器や、固体素子を用いたマイクロ波発振器等を適宜用いることができる。
In the present invention, the output, frequency, and irradiation method of the microwave to be irradiated are not particularly limited, and may be controlled so that the reaction temperature can be maintained within a predetermined range. The frequency of the microwave is usually 0.3 GHz to 30 GHz. In the frequency range of less than 0.3 GHz or more than 30 GHz, the cyclization reaction is insufficient and the effect of promoting the formation of cyclic ketone is insufficient.
In the microwave irradiation in the reaction of the present invention, various commercially available devices equipped with a contact type or non-contact type temperature sensor can be used. Furthermore, the output of microwave irradiation, the type of cavity (multimode, single mode), the form of irradiation (continuous, intermittent), etc. can be arbitrarily determined according to the scale and type of reaction.
As the microwave oscillator, a microwave oscillator such as a magnetron, a microwave oscillator using a solid element, or the like can be used as appropriate.
本発明の方法で生成した環状ケトンの精製は、クロマトグラフィー、蒸留、再結晶等の通常用いられる手段により容易に達せられる。 Purification of the cyclic ketone produced by the method of the present invention can be easily achieved by commonly used means such as chromatography, distillation, recrystallization and the like.
次に、本発明を実施例および比較例によりさら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。
（実施例１）
４−フェニル酪酸（Ｉ−ａ） ０．８０ｍｍｏｌ、Ｈ−Ｂｅｔａ型ゼオライト ＨＳＺ−９４０ＨＯＡ（東ソー社製） １００ｍｇ、１，２−ジクロロベンゼン １．０ｍｌの混合物を反応管に入れ、放射温度計を備えたマイクロ波照射装置（ＣＥＭ社製、Ｄｉｓｃｏｖｅｒ、シングルモード型）を用いて、攪拌しながら２２０℃で１０分反応させた。生成物をガスクロマトグラフ及びガスクロマトグラフ質量分析計で分析した結果、１−テトラロン（ＩＩ−ａ）が８９％の収率で生成したことがわかった。
EXAMPLES Next, although an Example and a comparative example demonstrate this invention further more concretely, this invention is not limited to these Examples.
Example 1
4-phenylbutyric acid (I-a) 0.80 mmol, H-Beta type zeolite HSZ-940HOA (manufactured by Tosoh Corporation) 100 mg, 1,2-dichlorobenzene 1.0 ml is put in a reaction tube, and equipped with a radiation thermometer Using a microwave irradiation apparatus (CEM, Discover, single mode type), the mixture was reacted at 220 ° C. for 10 minutes with stirring. As a result of analyzing the product with a gas chromatograph and a gas chromatograph mass spectrometer, it was found that 1-tetralone (II-a) was produced in a yield of 89%.
（実施例２）
Ｉ−ａの代わりに４−（４−トリル）酪酸（Ｉ−ｂ）を用いて、実施例１と同様に２００℃で１０分の反応を行った。生成物をガスクロマトグラフ及びガスクロマトグラフ質量分析計で分析した結果、７−メチル−１−テトラロン（ＩＩ−ｂ）が９３％の収率で生成したことがわかった。
反応混合物を遠心分離器にかけて上澄みを分離し、アセトン（２ｍｌ×３回）で残存固体を洗浄した。上澄みと洗浄液を合わせて減圧濃縮し、濃縮物をカラムクラマトグラフィー（シリカゲル、ヘキサン：酢酸エチル＝７：１）で精製すると、ＩＩ−ｂが８５％の収率で得られた。
(Example 2)
Using 4- (4-tolyl) butyric acid (Ib) instead of Ia, the reaction was carried out at 200 ° C. for 10 minutes in the same manner as in Example 1. As a result of analyzing the product with a gas chromatograph and a gas chromatograph mass spectrometer, it was found that 7-methyl-1-tetralone (II-b) was produced in a yield of 93%.
The reaction mixture was centrifuged to separate the supernatant, and the remaining solid was washed with acetone (2 ml × 3 times). The supernatant and washing solution were combined and concentrated under reduced pressure, and the concentrate was purified by column chromatography (silica gel, hexane: ethyl acetate = 7: 1) to obtain II-b in a yield of 85%.
（実施例３）
Ｉ−ａの代わりに４−（４−フルオロフェニル）酪酸（Ｉ−ｃ）を用いて、実施例１と同様に２２０℃で１０分の反応を行った。生成物をガスクロマトグラフ及びガスクロマトグラフ質量分析計で分析した結果、７−フルオロ−１−テトラロン（ＩＩ−ｃ）が９５％の収率で生成したことがわかった。
この反応混合物について、実施例２と同様の精製操作を行うと、ＩＩ−ｃが８５％の収率で得られた。
(Example 3)
Using 4- (4-fluorophenyl) butyric acid (Ic) instead of Ia, the reaction was carried out at 220 ° C. for 10 minutes in the same manner as in Example 1. As a result of analyzing the product with a gas chromatograph and a gas chromatograph mass spectrometer, it was found that 7-fluoro-1-tetralone (II-c) was produced in a yield of 95%.
When this reaction mixture was purified in the same manner as in Example 2, II-c was obtained in a yield of 85%.
（実施例４）
Ｉ−ａの代わりに４−（４−ニトロフェニル）酪酸（Ｉ−ｄ）を用いて、実施例１と同様に２２０℃で６０分の反応を行った。生成物をガスクロマトグラフ及びガスクロマトグラフ質量分析計で分析した結果、７−ニトロ−１−テトラロン（ＩＩ−ｄ）が１５％の収率で生成したことがわかった。
Example 4
Using 4- (4-nitrophenyl) butyric acid (Id) instead of Ia, a reaction was carried out at 220 ° C. for 60 minutes in the same manner as in Example 1. As a result of analyzing the product with a gas chromatograph and a gas chromatograph mass spectrometer, it was found that 7-nitro-1-tetralone (II-d) was produced in a yield of 15%.
（実施例５〜３８）
原料の芳香環置換アルカン酸や反応条件（触媒、装置、温度等）を変えて、実施例１と同様に反応及び分析を行い、生成した環状ケトンの収率を測定した結果を表１に示す。
I-b：４−（４−トリル）酪酸、
I-c：４−（４−フルオロフェニル）酪酸、
I-d：４−（４−ニトロフェニル）酪酸、
I-e：４−（４−メトキシフェニル）酪酸、
I-f：４−（２，５−ジメトキシフェニル）酪酸、
I-g：３−フェニルプロピオン酸、
I-h：５−フェニル吉草酸、
I-i：４−（３−チエニル）酪酸
２）930HOA：Ｈ−Ｂｅｔａ型ゼオライト ＨＳＺ−９３０ＨＯＡ（東ソー社製）、
940HOA：Ｈ−Ｂｅｔａ型ゼオライト ＨＳＺ−９４０ＨＯＡ（東ソー社製）、
830HOA：Ｈ−ＺＳＭ−５型ゼオライト ＨＳＺ−８３０ＨＯＡ（東ソー社製）、
840HOA：Ｈ−ＺＳＭ−５型ゼオライト ＨＳＺ−８４０ＨＯＡ（東ソー社製）、
620HOA：Ｈ−Ｍｏｒｄｅｎｉｔｅ型ゼオライト ＨＳＺ−６２０ＨＯＡ（東ソー社製）、
341HUA：Ｈ−Ｙ型ゼオライト ＨＳＺ−３４１ＨＯＡ（東ソー社製）、
360HUA：Ｈ−Ｙ型ゼオライト ＨＳＺ−３６０ＨＵＡ（東ソー社製）、
390HUA：Ｈ−Ｙ型ゼオライト ＨＳＺ−３９０ＨＯＡ（東ソー社製）、
SAPO-11：Ｈ−ＳＡＰＯ型ゼオライト ＳＡＰＯ−１１（日揮ユニバーサル社製）、
SAC-13：シリカ担持ナフィオン ＳＡＣ−１３（アルドリッチ社製）、
NR50：ナフィオン ＮＲ５０（アルドリッチ社製）、
Al-mont：Ａｌ３＋−モンモリロナイト
３）1,2-DCB：１，２−ジクロロベンゼン、
1,3-DCB：１，３−ジクロロベンゼン、
TCB：１，２，４−トリクロロベンゼン
CB：クロロベンゼン
４）A:Ｄｉｓｃｏｖｅｒ（ＣＥＭ社製）、B：Ｉｎｉｔｉａｔｏｒ（バイオタージ社製）
５）II-a：１−テトラロン、
II-b：７−メチル−１−テトラロン、
II-c：７−フルオロ−１−テトラロン、
II-d：７−ニトロ−１−テトラロン、
II-e：７−メトキシ−１−テトラロン、
II-f：５，８−ジメトキシ−１−テトラロン、
II-g：１−インダノン、
II-h：１−ベンゾスベロン、
II-i：４−オキソ−４，５，６，７−テトラヒドロチアナフテン
(Examples 5-38)
Table 1 shows the results of measuring the yield of the produced cyclic ketone by carrying out the reaction and analysis in the same manner as in Example 1 by changing the raw material aromatic ring-substituted alkanoic acid and the reaction conditions (catalyst, apparatus, temperature, etc.). .
Ib: 4- (4-Tolyl) butyric acid,
Ic: 4- (4-fluorophenyl) butyric acid,
Id: 4- (4-nitrophenyl) butyric acid,
Ie: 4- (4-methoxyphenyl) butyric acid,
If: 4- (2,5-dimethoxyphenyl) butyric acid,
Ig: 3-phenylpropionic acid,
Ih: 5-phenylvaleric acid,
Ii: 4- (3-thienyl) butyric acid 2) 930HOA: H-Beta type zeolite HSZ-930HOA (manufactured by Tosoh Corporation),
940HOA: H-Beta type zeolite HSZ-940HOA (manufactured by Tosoh Corporation),
830HOA: H-ZSM-5 type zeolite HSZ-830HOA (manufactured by Tosoh Corporation),
840HOA: H-ZSM-5 type zeolite HSZ-840HOA (manufactured by Tosoh Corporation),
620HOA: H-Mordenite type zeolite HSZ-620HOA (manufactured by Tosoh Corporation),
341HUA: HY type zeolite HSZ-341HOA (manufactured by Tosoh Corporation),
360HUA: H-Y type zeolite HSZ-360HUA (manufactured by Tosoh Corporation),
390HUA: HY type zeolite HSZ-390HOA (manufactured by Tosoh Corporation),
SAPO-11: H-SAPO type zeolite SAPO-11 (manufactured by JGC Universal),
SAC-13: silica-carrying Nafion SAC-13 (manufactured by Aldrich),
NR50: Nafion NR50 (manufactured by Aldrich),
Al-mont: Al 3+ -montmorillonite 3) 1,2-DCB: 1,2-dichlorobenzene,
1,3-DCB: 1,3-dichlorobenzene,
TCB: 1,2,4-trichlorobenzene
CB: Chlorobenzene 4) A: Discover (CEM), B: Initiator (Biotage)
5) II-a: 1-tetralone,
II-b: 7-methyl-1-tetralone,
II-c: 7-fluoro-1-tetralone,
II-d: 7-nitro-1-tetralone,
II-e: 7-methoxy-1-tetralone,
II-f: 5,8-dimethoxy-1-tetralone,
II-g: 1-Indanone,
II-h: 1-benzosuberone,
II-i: 4-oxo-4,5,6,7-tetrahydrothianaphthene
（比較例１）
マイクロ波照射装置の代わりにオイルバスを用いる他は実施例３と同様に反応及び分析を行った結果、ＩＩ−ｃの収率は２０％であり、実施例３で得られた収率の９５％よりも低いものであった。このことは、マイクロ波照射の反応が、同じ反応温度・時間でのオイルバスによる通常加熱の反応に比べ、ＩＩ−ｃを短時間で収率よく与えることを示している。
(Comparative Example 1)
The reaction and analysis were conducted in the same manner as in Example 3 except that an oil bath was used instead of the microwave irradiation apparatus. As a result, the yield of II-c was 20%, which was 95% of the yield obtained in Example 3. %. This shows that the reaction of microwave irradiation gives II-c in a short time with a high yield as compared with the reaction of normal heating with an oil bath at the same reaction temperature and time.
（比較例２〜１８）
他の実施例において、比較例１と同様に、オイルバスでの反応及び分析を行った結果を、対応する実施例の結果と共に表２に示す。
In other examples, similar to Comparative Example 1, the results of the reaction and analysis in the oil bath are shown in Table 2 together with the results of the corresponding examples.
いずれの比較例においても、生成した環状ケトンの収率は対応する実施例の値よりも低く、マイクロ波照射を用いることにより、原料や触媒の種類等の反応条件に関わりなく、環状ケトンをより効率的に製造できることが示された。 In any of the comparative examples, the yield of the produced cyclic ketone is lower than the value of the corresponding example, and by using microwave irradiation, the cyclic ketone can be obtained more regardless of the reaction conditions such as the type of raw material and catalyst. It was shown that it can be manufactured efficiently.
本発明の方法により、各種医・農薬やその製造中間体として有用な環状ケトンを、より効率的かつ安全に製造できる。特に、本発明により得られるテトラロンやインダノン等の誘導体にはさまざまな薬理活性が知られているため利用価値が高く、本発明の工業的意義は多大である。 By the method of the present invention, it is possible to more efficiently and safely produce cyclic ketones useful as various medicines / agrochemicals and production intermediates thereof. In particular, derivatives such as tetralone and indanone obtained by the present invention have high utility value because various pharmacological activities are known, and the industrial significance of the present invention is great.
Claims (4)
で表される芳香環置換アルカン酸を、触媒の存在下で、マイクロ波を照射して反応させることを特徴とする、下記の一般式（ＩＩ）
で表される環状ケトンの製造方法。 The following general formula (I)
Wherein the aromatic ring-substituted alkanoic acid is reacted by irradiation with microwaves in the presence of a catalyst.
The manufacturing method of cyclic ketone represented by these.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2010101120A1 (en) * | 2009-03-02 | 2010-09-10 | 国立大学法人 鹿児島大学 | Apparatus for producing aromatic hydrocarbons or ketone compounds, apparatus for producing levulinic acid, apparatus for separating levulinic acid, and apparatus for producing hydrocarbons from levulinic acid |
| JP2014196285A (en) * | 2013-03-05 | 2014-10-16 | 田岡化学工業株式会社 | Method of producing fluorenone derivative |
| WO2019044946A1 (en) * | 2017-08-31 | 2019-03-07 | 第一三共株式会社 | Novel method for producing antibody-drug conjugate |
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