JP3279801B2 - New method for producing carboxylic acid ester - Google Patents
New method for producing carboxylic acid esterInfo
- Publication number
- JP3279801B2 JP3279801B2 JP03966894A JP3966894A JP3279801B2 JP 3279801 B2 JP3279801 B2 JP 3279801B2 JP 03966894 A JP03966894 A JP 03966894A JP 3966894 A JP3966894 A JP 3966894A JP 3279801 B2 JP3279801 B2 JP 3279801B2
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- general formula
- represented
- acid ester
- substituent
- 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 - Fee Related
Links
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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明はカルボン酸エステルの新
規な製造方法に関する。The present invention relates to a novel process for producing carboxylic acid esters.
【０００２】[0002]
【従来の技術】種々の生理活性物質にはエステル残基を
含む化合物が数多く知られており、エステル合成反応
は、有機合成上極めて重要な反応である。2. Description of the Related Art Numerous compounds containing ester residues are known among various physiologically active substances, and the ester synthesis reaction is a very important reaction in organic synthesis.
【０００３】従来、対応するカルボン酸とアルコールか
ら、カルボン酸エステルを合成する方法としては以下に
示す方法が一般的である。Heretofore, as a method for synthesizing a carboxylic acid ester from a corresponding carboxylic acid and alcohol, the following method is generally used.
【０００４】即ち、（１）カルボン酸とアルコールと
を、触媒量のプロトン酸又はルイス酸存在下に加熱する
方法、或いは、（２）当量以上のプロトン酸又はルイス
酸を用いる方法、並びに（３）塩基性条件下でカルボン
酸の活性誘導体とアルコールから合成する方法等であ
る。That is, (1) a method in which a carboxylic acid and an alcohol are heated in the presence of a catalytic amount of a protonic acid or a Lewis acid, (2) a method in which an equivalent amount or more of a protonic acid or a Lewis acid is used, and A) synthesis from an active derivative of a carboxylic acid and an alcohol under basic conditions.
【０００５】しかし、種々の生理活性物質においては、
近年、ますます複雑な構造を持つ不安定な化合物が合成
目標として取り上げられることが多く、より中性に近い
温和な条件下で、しかも当量のカルボン酸とアルコール
から円滑に進行するエステル合成法が医薬品合成上から
も望まれている。However, in various physiologically active substances,
In recent years, unstable compounds with increasingly complex structures are often taken up as synthesis targets, and ester synthesis methods that proceed smoothly from mild carboxylic acids and alcohols under mild conditions close to neutrality have been developed. It is also desired from the viewpoint of drug synthesis.
【０００６】当量のカルボン酸とアルコールから、エス
テルを得る簡便な合成法に関する知見は未だ数少なく、
例えば、１−アルキル−２−ハロピリジニウム塩による
エステル化反応（T.Mukaiyama,Angew.Chem.,Int.ED.Eng
l,18,707(1979)）及び２，４，６−トリクロロベンゾイ
ルクロリドを用い、塩基性条件下、混合酸無水物を経由
する方法（K.Hirata,H.Saeki,T.Katsuki,and M.Yamaguc
hi,Bull.Chem.Soc.Japan.,52,1989(1979)）が挙げられ
る。しかし、これらの方法では、不飽和エステル類を、
異性化を伴うことなく純粋に得ることが困難なことも知
られている。エステルを得る簡便な合成法の開発は、有
機合成上未だ残された大きな課題である。[0006] There are still few findings on a simple synthesis method for obtaining an ester from an equivalent amount of a carboxylic acid and an alcohol.
For example, an esterification reaction with a 1-alkyl-2-halopyridinium salt (T. Mukaiyama, Angew. Chem., Int. ED. Eng.
1,18,707 (1979)) and 2,4,6-trichlorobenzoyl chloride via a mixed acid anhydride under basic conditions (K. Hirata, H. Saeki, T. Katsuki, and M. Yamaguc).
hi, Bull. Chem. Soc. Japan., 52, 1989 (1979)). However, in these methods, the unsaturated esters are
It is also known that it is difficult to obtain purely without isomerization. The development of a simple synthetic method for obtaining an ester is a major problem left in organic synthesis.
【０００７】また本発明者らは、先に、カルボン酸トリ
アルキルシリルエステル誘導体とトリアルキルシリルエ
ーテル誘導体とを、一般式（４） （Ｒ3ＣＯ）2Ｏ （４） （式中、Ｒ3は置換基を有していてもよいアリール基を
示す）で表されるカルボン酸無水物と触媒量のカチオン
性触媒を共存させることにより高い収率でエステル誘導
体を得る手法を開発している（特開平５−２８６８９４
号）。[0007] The present inventors have previously carboxylic acid trialkylsilyl ester derivative and a trialkylsilyl ether derivatives of the general formula (4) (R 3 CO) 2 O (4) ( wherein, R 3 Represents an aryl group which may have a substituent), and a method for obtaining an ester derivative with a high yield by coexisting a carboxylic anhydride represented by the formula (1) and a catalytic amount of a cationic catalyst has been developed ( JP-A-5-286894
issue).
【０００８】[0008]
【発明が解決しようとする課題】本発明の課題は、アル
コールと、当量もしくは小過剰のカルボン酸から直接的
に、温和な条件下で効率良く、カルボン酸エステルを製
造する方法を提供することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide a method for efficiently producing a carboxylic acid ester directly from an alcohol and an equivalent or a small excess of a carboxylic acid under mild conditions. is there.
【０００９】[0009]
【課題を解決するための手段】本発明者らは、上記課題
を解決するために鋭意研究を重ねた結果、アルコール
と、当量もしくは小過剰のカルボン酸を反応させ、カル
ボン酸エステルを製造する際に、前記一般式（４）で表
されるカルボン酸無水物及び特定のハロゲノアルキルシ
ランと触媒量のカチオン性触媒を共存させることによ
り、温和な条件下で、効率的にカルボン酸エステルを製
造できることを見出し、発明を完成した。Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that when an alcohol is reacted with an equivalent or a small excess of a carboxylic acid to produce a carboxylic acid ester. The carboxylic acid ester represented by the general formula (4) and a specific halogenoalkylsilane in the presence of a catalytic amount of a cationic catalyst to efficiently produce a carboxylic acid ester under mild conditions. And completed the invention.
【００１０】すなわち、本発明は、一般式（１） Ｒ1ＣＯＯＨ （１） （式中、Ｒ1は置換基を有していてもよいアルキル基又
はアリール基を示す）で表されるカルボン酸と、一般式
（２） Ｒ2ＯＨ （２） （式中、Ｒ2は置換基を有していてもよいアルキル基又
はアリール基を示す）で表されるアルコールとを反応さ
せて、一般式（３） Ｒ1ＣＯＯＲ2 （３） （式中、Ｒ1及びＲ2は前記定義に同じ）で表されるカル
ボン酸エステルを製造する方法において、一般式（４） （Ｒ3ＣＯ）2Ｏ （４） （式中、Ｒ3は置換基を有していてもよいアリール基を
示す）で表されるカルボン酸無水物及び一般式（５） （Ｒ4）nＳｉＸ(4-n) （５） （式中、Ｒ4は低級アルキル基を、Ｘはハロゲン原子
を、ｎは１〜３の整数を示す）で表されるハロゲノアル
キルシランと触媒量のカチオン性触媒を共存させること
を特徴とするカルボン酸エステルの製造方法に関するも
のである。That is, the present invention provides a carboxylic acid represented by the general formula (1) R 1 COOH (1) (wherein R 1 represents an alkyl group or an aryl group which may have a substituent). And an alcohol represented by the general formula (2) R 2 OH (2) (wherein R 2 represents an alkyl group or an aryl group which may have a substituent), (3) R 1 COOR 2 (3) (wherein R 1 and R 2 are the same as defined above) in the method for producing a carboxylic acid ester represented by the general formula (4) (R 3 CO) 2 O (4) wherein R 3 represents an aryl group which may have a substituent, and a carboxylic anhydride represented by the general formula (5): (R 4 ) n SiX (4-n) ( 5) (wherein halogen of the R 4 is a lower alkyl group, X is a halogen atom, n represents is represented by an integer of 1 to 3) A process for producing a carboxylic acid ester, characterized in that the coexistence of an alkyl silane and a catalytic amount of a cationic catalyst.
【００１１】本発明方法の、出発物質であるカルボン酸
の一般式（１）中のＲ1とアルコールの一般式（２）中
のＲ2は、置換基を有してもよいアルキル基又はアリー
ル基であるが、基本的にはいかなる置換基でもよく、一
般にエステル化反応が困難とされている置換基を有する
ものでも本発明方法によればエステル化が可能である。In the method of the present invention, R 1 in the general formula (1) of the starting carboxylic acid and R 2 in the general formula (2) of the alcohol are an alkyl group or aryl which may have a substituent. Although it is a group, basically any substituent may be used. Esterification is possible according to the method of the present invention, even if the substituent has a substituent which is generally difficult to esterify.
【００１２】本発明方法において一般式（２）のアルコ
ールに対する一般式（１）のカルボン酸は、当量もしく
は小過剰量でよい。In the method of the present invention, the carboxylic acid of the general formula (1) relative to the alcohol of the general formula (2) may be in an equivalent amount or a small excess.
【００１３】本発明方法のエステル化反応において共存
させるカルボン酸無水物の一般式（４）の式中のＲ
3は、電子吸引性基を有するアリール基が好ましく、特
にフッ素原子、塩素原子等のハロゲン原子、トリクロル
メチル基、トリフルオロメチル基等のハロゲン置換低級
アルキル基等で置換されたフェニル基が好ましい。一般
式（４）のカルボン酸無水物としては、無水４−トリフ
ルオロメチル安息香酸が反応収率の点で最も好ましい。
一般式（４）のカルボン酸無水物の添加量は、基質であ
る一般式（１）のカルボン酸に対して、９０〜１２０モ
ル％、好ましくは、１００モル％である。The carboxylic anhydride coexisting in the esterification reaction of the method of the present invention is represented by R in the formula of the general formula (4).
3 is preferably an aryl group having an electron-withdrawing group, particularly preferably a phenyl group substituted with a halogen atom such as a fluorine atom or a chlorine atom, or a halogen-substituted lower alkyl group such as a trichloromethyl group or a trifluoromethyl group. As the carboxylic anhydride of the general formula (4), 4-trifluoromethylbenzoic anhydride is most preferable in terms of the reaction yield.
The amount of the carboxylic anhydride of the general formula (4) to be added is 90 to 120 mol%, preferably 100 mol%, based on the carboxylic acid of the general formula (1) as a substrate.
【００１４】本発明方法において、一般式（４）のカル
ボン酸無水物とともに共存させる一般式（５）のハロゲ
ノアルキルシランの式中のＲ4は炭素数１〜６の低級ア
ルキル基で、例えばメチル基、エチル基、ｔ−ブチル基
等が好ましく、Ｘはハロゲン原子、例えば、フッ素、塩
素、臭素、ヨウ素等が好ましい。一般式（５）のハロゲ
ノアルキルシランとしては、クロロトリメチルシラン
が、価格及び汎用性の点で最も好ましい。一般式（５）
の化合物の添加量は、基質である一般式（１）のカルボ
ン酸に対して０．１〜５００モル％、好ましくは１〜２
００モル％使用することが好ましい。０．１モル％未満
では充分な効果が得られず、５００モル％を超えて加え
ても収率に変わりはなく、製造コストが嵩むだけであ
る。In the process of the present invention, R 4 in the halogenoalkylsilane of the general formula (5) coexisting with the carboxylic anhydride of the general formula (4) is a lower alkyl group having 1 to 6 carbon atoms, for example, methyl X, a halogen atom, for example, fluorine, chlorine, bromine, iodine and the like are preferable. As the halogenoalkylsilane of the general formula (5), chlorotrimethylsilane is most preferable in terms of cost and versatility. General formula (5)
The compound is added in an amount of 0.1 to 500 mol%, preferably 1 to 2 mol%, based on the carboxylic acid of the general formula (1) as a substrate.
It is preferable to use 00 mol%. If the amount is less than 0.1 mol%, a sufficient effect cannot be obtained, and if it exceeds 500 mol%, the yield does not change and only the production cost increases.
【００１５】本発明において用いるカチオン性触媒と
は、四塩化チタン、塩化ハフニウム、塩化ジルコニウ
ム、塩化アルミニウム、塩化ガリウム、塩化インジウ
ム、塩化鉄、塩化スズ（ＩＩ）等の各種ルイス酸、又は
過塩素酸銀、トリフルオロメタンスルホン酸銀等の銀塩
と各種ルイス酸との複合塩、及びトリフルオロメタンス
ルホン酸スズ（ＩＩ）等が好ましく、基質である一般式
（１）の化合物に対して０．０１〜１００モル％使用す
ることが好ましい。０．０１モル％未満では充分な触媒
効果が得られず、１００モル％を超えて加えても触媒効
果に変わりはなく、製造コストが嵩むだけである。The cationic catalyst used in the present invention includes various Lewis acids such as titanium tetrachloride, hafnium chloride, zirconium chloride, aluminum chloride, gallium chloride, indium chloride, iron chloride and tin (II) chloride, or perchloric acid. Silver, a complex salt of a silver salt such as silver trifluoromethanesulfonate and various Lewis acids, and tin (II) trifluoromethanesulfonate are preferable, and the amount of the compound is 0.01 to 0.01% based on the compound of the general formula (1) as a substrate. It is preferable to use 100 mol%. If it is less than 0.01 mol%, a sufficient catalytic effect cannot be obtained, and if it exceeds 100 mol%, the catalytic effect remains unchanged, and only the production cost increases.
【００１６】本発明方法は、アセトニトリル、エーテ
ル、１，２−ジクロルエタン、ベンゼン、トルエン、ジ
クロルメタン等の反応に関与しない溶媒中で、０〜５０
℃、好ましくは１０〜３０℃の温度で行えばよい。The process of the present invention is carried out in a solvent which does not participate in a reaction such as acetonitrile, ether, 1,2-dichloroethane, benzene, toluene, dichloromethane, etc., from 0 to 50.
C, preferably at a temperature of 10 to 30C.
【００１７】本発明方法によれば、通常の混合酸無水物
を用いたエステル化反応で副生する不純物（上記一般式
で言えば、一般式（２）で表される化合物と一般式
（４）で表される化合物が反応したもの）はまったく得
られず、高い化学選択性を示す。According to the method of the present invention, impurities produced as a by-product in an esterification reaction using a common mixed acid anhydride (in the above general formula, the compound represented by the general formula (2) and the compound represented by the general formula (4) ) Is not obtained at all and shows high chemical selectivity.
【００１８】[0018]
【実施例】以下に実施例を示し、本発明方法の有用性を
示すが、本発明は実施例に限定されるものではない。EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples.
【００１９】実施例１ Embodiment 1
【００２０】[0020]
【化１】 Embedded image
【００２１】アルゴン気流下、過塩素酸銀（７．７ｍ
ｇ，０．０３７ｍＭ）、四塩化チタン（３．５ｍｇ、
０．０１８５ｍＭ）及びクロロトリメチルシラン（１０
１ｍｇ，０．９３ｍＭ）を１０ｍｌのジクロルメタンに
懸濁させた。これにジクロルメタン７．５ｍｌに溶解し
た３−フェニルプロピオン酸（３０７ｍｇ、２．０４ｍ
Ｍ）及び４−トリフルオロメチル安息香酸無水物（７４
０ｍｇ、２．０４ｍＭ）の混液を加えた。次いで、ジク
ロルメタン２．５ｍｌに溶解した１−メチル−３−フェ
ニルプロパノール（２７８ｍｇ、１．８５ｍＭ）を加え
て、室温で３時間撹拌した。反応液に飽和炭酸水素ナト
リウム水溶液を加えた後、ジクロルメタンで抽出した。
有機層を無水硫酸ナトリウムで乾燥後、濾液を減圧濃縮
した。残渣をシリカゲル薄層クロマトグラフィー（展開
溶媒ヘキサン：酢酸エチル＝９：１）にて精製し、目的
物の３−フェニルプロピオン酸１−メチル−３−フェニ
ルプロピルエステル（５１８ｍｇ、収率９９％）を得
た。In an argon stream, silver perchlorate (7.7 m
g, 0.037 mM), titanium tetrachloride (3.5 mg,
0.0185 mM) and chlorotrimethylsilane (10
(1 mg, 0.93 mM) was suspended in 10 ml of dichloromethane. To this, 3-phenylpropionic acid (307 mg, 2.04 m) dissolved in 7.5 ml of dichloromethane was added.
M) and 4-trifluoromethylbenzoic anhydride (74
(0 mg, 2.04 mM). Next, 1-methyl-3-phenylpropanol (278 mg, 1.85 mM) dissolved in 2.5 ml of dichloromethane was added, and the mixture was stirred at room temperature for 3 hours. After adding a saturated aqueous solution of sodium hydrogen carbonate to the reaction solution, extraction was performed with dichloromethane.
After the organic layer was dried over anhydrous sodium sulfate, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel thin layer chromatography (developing solvent: hexane: ethyl acetate = 9: 1) to obtain the desired product, 3-phenylpropionic acid 1-methyl-3-phenylpropyl ester (518 mg, yield 99%). Was.
【００２２】ＮＭＲ（ＣＤＣｌ3、ＴＭＳ標準） δＰ
ＰＭ：７．３１〜７．１１（１０Ｈ，ｍ）、４．９９〜
４．８８（１Ｈ，ｍ）、２．９５（２Ｈ，ｔ，Ｊ＝７．
９Ｈｚ）、２．９９〜２．５１（４Ｈ，ｍ）、１．９６
〜１．７２（２Ｈ，ｍ）、１．２１（３Ｈ，ｄ，Ｊ＝
６．３Ｈｚ）。NMR (CDCl 3 , TMS standard) δP
PM: 7.31 to 7.11 (10H, m), 4.99 to
4.88 (1H, m), 2.95 (2H, t, J = 7.
9 Hz), 2.99 to 2.51 (4H, m), 1.96
~ 1.72 (2H, m), 1.21 (3H, d, J =
6.3 Hz).
【００２３】実施例２〜６ 実施例１に準じて、一般式（５）で表される化合物（ク
ロロトリメチルシラン）の添加量及び一般式（４）の化
合物を変更して反応を実施した。結果を表１に示す。 Examples 2 to 6 According to Example 1, the reaction was carried out by changing the amount of the compound represented by the general formula (5) (chlorotrimethylsilane) and the compound of the general formula (4). Table 1 shows the results.
【００２４】[0024]
【表１】 [Table 1]
【００２５】実施例７〜１９ 実施例１に準じて、一般式（１）のカルボン酸及び一般
式（２）のアルコールを変更して反応を実施した。結果
を表２に示す。 Examples 7 to 19 The reaction was carried out according to Example 1, except that the carboxylic acid of the general formula (1) and the alcohol of the general formula (2) were changed. Table 2 shows the results.
【００２６】[0026]
【表２】 [Table 2]
【００２７】参考例１ クロロトリメチルシランを添加しない以外は、実施例１
の方法に準じて反応を行った。目的物の収率は８８％で
あった。 Reference Example 1 Example 1 was repeated except that chlorotrimethylsilane was not added.
The reaction was carried out according to the method described above. The yield of the desired product was 88%.
【００２８】[0028]
【発明の効果】以上のように、本発明方法によればほぼ
等量のアルコールとカルボン酸から、温和な条件下で、
高収率でカルボン酸エステルを製造することが可能であ
る。本合成法は極めて簡便でありかつ効率的であるとい
う利点を持ち合わせているため、有機合成化学上有用な
手法になり得るものである。As described above, according to the method of the present invention, almost equal amounts of alcohol and carboxylic acid are produced under mild conditions.
It is possible to produce carboxylic esters in high yield. Since this synthesis method has the advantages of being extremely simple and efficient, it can be a useful technique in organic synthetic chemistry.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ // Ｂ０１Ｊ 31/26 Ｂ０１Ｊ 31/26 Ｘ Ｃ０７Ｂ 61/00 ３００ Ｃ０７Ｂ 61/00 ３００ (72)発明者 宮下 三朝 東京都新宿区神楽坂１丁目３番 東京理 科大学理学部内 (56)参考文献 特開 平６−345687（ＪＰ，Ａ) 特開 平５−286894（ＪＰ，Ａ) 特開 昭50−140405（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 67/08 C07C 69/24 C07C 69/616 C07C 69/618 C07C 69/75 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI // B01J 31/26 B01J 31/26 X C07B 61/00 300 C07B 61/00 300 (72) Inventor Misasa Miyashita Shinjuku-ku, Tokyo 1-3-3 Kagurazaka, Tokyo University of Science Faculty of Science (56) References JP-A-6-345687 (JP, A) JP-A-5-286894 (JP, A) JP-A-50-140405 (JP, A) ( 58) Field surveyed (Int. Cl. 7 , DB name) C07C 67/08 C07C 69/24 C07C 69/616 C07C 69/618 C07C 69/75
Claims (3)
はアリール基を示す）で表されるカルボン酸と、一般式
（２） Ｒ2ＯＨ （２） （式中、Ｒ2は置換基を有していてもよいアルキル基又
はアリール基を示す）で表されるアルコールとを反応さ
せて、一般式（３） Ｒ1ＣＯＯＲ2 （３） （式中、Ｒ1及びＲ2は前記定義に同じ）で表されるカル
ボン酸エステルを製造する方法において、一般式（４） （Ｒ3ＣＯ）2Ｏ （４） （式中、Ｒ3は置換基を有していてもよいアリール基を
示す）で表されるカルボン酸無水物及び一般式（５） （Ｒ4）nＳｉＸ(4-n) （５） （式中、Ｒ4は低級アルキル基を、Ｘはハロゲン原子
を，ｎは１〜３の整数を示す）で表されるハロゲノアル
キルシランと触媒量のカチオン性触媒を共存させること
を特徴とするカルボン酸エステルの製造方法。1. A carboxylic acid represented by the general formula (1): R 1 COOH (1) (wherein R 1 represents an alkyl group or an aryl group which may have a substituent); (2) R 2 OH (2) (wherein R 2 represents an alkyl group or an aryl group which may have a substituent), and reacted with an alcohol represented by the general formula (3): 1 COOR 2 (3) (wherein R 1 and R 2 are the same as defined above) in the method for producing a carboxylic acid ester represented by the general formula (4) (R 3 CO) 2 O (4) ( Wherein R 3 represents an aryl group which may have a substituent, and a carboxylic acid anhydride represented by the general formula (5): (R 4 ) n SiX (4-n) (5) among, R 4 is a lower alkyl group, X is a halogen atom, n represents tactile and halogenoalkylsilanes represented by an integer of 1 to 3) Method for producing a carboxylic acid ester, characterized in that the coexistence of the amount of the cationic catalyst.
フルオロメチル安息香酸である請求項１記載のカルボン
酸エステルの製造方法。2. The method for producing a carboxylic acid ester according to claim 1, wherein the compound of the general formula (4) is 4-trifluoromethylbenzoic anhydride.
チルシランである請求項１記載のカルボン酸エステルの
製造方法。3. The method according to claim 1, wherein the compound of the general formula (5) is chlorotrimethylsilane.
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|---|---|---|---|
| JP03966894A JP3279801B2 (en) | 1994-03-10 | 1994-03-10 | New method for producing carboxylic acid ester |
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| JP3279801B2 true JP3279801B2 (en) | 2002-04-30 |
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