JP3188930B2 - Method for producing 1,4-dihydroxy-2-naphthoic acid aryl ester - Google Patents
Method for producing 1,4-dihydroxy-2-naphthoic acid aryl esterInfo
- Publication number
- JP3188930B2 JP3188930B2 JP35872391A JP35872391A JP3188930B2 JP 3188930 B2 JP3188930 B2 JP 3188930B2 JP 35872391 A JP35872391 A JP 35872391A JP 35872391 A JP35872391 A JP 35872391A JP 3188930 B2 JP3188930 B2 JP 3188930B2
- Authority
- JP
- Japan
- Prior art keywords
- naphthoic acid
- dihydroxy
- aryl ester
- reaction
- producing
- 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
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Landscapes
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は１，４−ジヒドロキシ−
２−ナフトエ酸アリールエステルの新規な製造方法に関
する。より詳細には、電極酸化を用いた１，４−ジヒド
ロキシ−２−ナフトエ酸アリールエステルの製造法に関
する。BACKGROUND OF THE INVENTION The present invention relates to 1,4-dihydroxy-
The present invention relates to a novel method for producing 2-naphthoic acid aryl esters. More specifically, the present invention relates to a method for producing 1,4-dihydroxy-2-naphthoic acid aryl ester using electrode oxidation.
【０００２】[0002]
【従来の技術】本発明の目的化合物である１，４−ジヒ
ドロキシ−２−ナフトエ酸アリールエステルは、染料、
顔料及び感光材料の中間物として有用な化合物であり、
工業的製造方法の開発が強く望まれている化合物であ
る。すなわち、１，４−ジヒドロキシ−２−ナフトエ酸
アリールエステルの製造法としては、１−ヒドロキシ−
２−ナフトエ酸を酸化して１，４−ジヒドロキシ−２−
ナフトエ酸とし、次いで得られた１，４−ジヒドロキシ
−２−ナフトエ酸をエステル化して１，４−ジヒドロキ
シ−２−ナフトエ酸アリールエステルを合成する方法が
考えられる。この方法の第１工程である１，４−ジヒド
ロキシ−２−ナフトエ酸の製造方法としては、１−ヒド
ロキシ−２−ナフトエ酸をＥｌｂｓ反応により酸化する
方法が知られている。この方法は、１−ヒドロキシ−２
−ナフトエ酸をアルカリ水溶液中過硫酸塩と反応させた
のち加水分解を行い、１，４−ジヒドロキシ−２−ナフ
トエ酸を合成する方法である。また、第２工程のエステ
ル化反応としては、１，４−ジヒドロキシ−２−ナフト
エ酸と、フェノール性水酸基を有する芳香族炭化水素類
（以下、便宜上、フェノール類という）とを酸触媒を用
いて脱水する方法が知られている。また、エステル化剤
としてアリール亜リン酸エステルを用いて１，４−ジヒ
ドロキシ−２−ナフトエ酸をエステル化して１，４−ジ
ヒドロキシ−２−ナフトエ酸アリールエステルを製造す
る方法が提案されている。BACKGROUND OF THE INVENTION Aryl 1,4-dihydroxy-2-naphthoate, the object compound of the present invention, is a dye,
A compound useful as an intermediate between pigments and photosensitive materials,
It is a compound for which the development of an industrial production method is strongly desired. That is, the production method of 1,4-dihydroxy-2-naphthoic acid aryl ester includes 1-hydroxy-
Oxidizing 2-naphthoic acid to give 1,4-dihydroxy-2-
A possible method is to synthesize naphthoic acid and then esterify the resulting 1,4-dihydroxy-2-naphthoic acid to synthesize 1,4-dihydroxy-2-naphthoic acid aryl ester. As a method for producing 1,4-dihydroxy-2-naphthoic acid, which is the first step of this method, a method of oxidizing 1-hydroxy-2-naphthoic acid by an Elbs reaction is known. This method uses 1-hydroxy-2
-A method in which naphthoic acid is reacted with a persulfate in an aqueous alkali solution and then hydrolyzed to synthesize 1,4-dihydroxy-2-naphthoic acid. In the esterification reaction in the second step, 1,4-dihydroxy-2-naphthoic acid and an aromatic hydrocarbon having a phenolic hydroxyl group (hereinafter, referred to as phenol for convenience) are used with an acid catalyst. Dehydration methods are known. Further, there has been proposed a method of producing 1,4-dihydroxy-2-naphthoic acid aryl ester by esterifying 1,4-dihydroxy-2-naphthoic acid using an aryl phosphite as an esterifying agent.
【０００３】[0003]
【発明が解決しようとする課題】上記の第１工程である
１−ヒドロキシ−２−ナフトエ酸のＥｌｂｓ反応による
酸化反応は、製造工程が煩雑であり、経時変化により選
択性が低下し工業的に有利な製造方法といえず、収率も
３０％程度に過ぎないという問題がある。他の酸化反応
についても、有用な反応はない。また、第２工程である
エステル化反応において、酸触媒として強酸を用いる方
法はカルボン酸を分解するため使用できない。そのた
め、脱水剤として三塩化燐、五塩化燐、オキシ塩化燐な
どを使用する方法が行われているが、原料であるフェノ
ール類を大過剰に使用しなければならず、廃水中のフェ
ノール類の除去など反応後の処理が難しく工業的な方法
といえない。また、エステル化剤としてアリール亜リン
酸エステルを用いる方法においては、副生成物として２
量体等も生成し、工業的見地からいっても問題は多い。
上記の従来の方法で、１−ヒドロキシ−２−ナフトエ酸
から１，４−ジヒドロキシ−２−ナフトエ酸アリールエ
ステルを合成した場合、精製等も含めると、トータル収
率は１０％程度に過ぎない。このように、本発明が目的
とする１，４−ジヒドロキシ−２−ナフトエ酸アリール
エステルの製造方法については現時点までまだ工業的に
確立されておらず、本発明の目的は１，４−ジヒドロキ
シ−２−ナフトエ酸アリールエステルの工業的な製造方
法を提供することにある。The oxidation reaction of the 1-hydroxy-2-naphthoic acid by the Elbs reaction, which is the first step, is complicated in the production process, and the selectivity is lowered due to aging, and the industrial process is industrially difficult. This is not an advantageous production method, and there is a problem that the yield is only about 30%. There are no useful reactions for other oxidation reactions. In the esterification reaction as the second step, a method using a strong acid as an acid catalyst cannot be used because carboxylic acid is decomposed. Therefore, methods using phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, etc. as a dehydrating agent have been used, but a large excess of phenols as a raw material must be used, and phenols in wastewater are reduced. Processing after the reaction such as removal is difficult and cannot be said to be an industrial method. In addition, in the method using an aryl phosphite as an esterifying agent, 2
It also produces monomers and the like, and there are many problems from an industrial point of view.
When 1,4-dihydroxy-2-naphthoic acid aryl ester is synthesized from 1-hydroxy-2-naphthoic acid by the above-mentioned conventional method, the total yield is only about 10%, including the purification. As described above, the production method of 1,4-dihydroxy-2-naphthoic acid aryl ester aimed at by the present invention has not yet been industrially established up to the present, and the object of the present invention is 1,4-dihydroxy-naphthoic acid. It is to provide an industrial production method of an aryl 2-naphthoate.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、１−ヒド
ロキシ−２−ナフトエ酸アリールエステルの陽極酸化を
行うと一段階で１，４−ジヒドロキシ−２−ナフトエ酸
アリールエステルが得られることを見出した。すなわち
本発明は、水性有機溶媒中、１−ヒドロキシ−２−ナフ
トエ酸アリールエステルを陽極酸化することからなる
１，４−ジヒドロキシ−２−ナフトエ酸アリールエステ
ルの製造方法であり、特に好ましくは、無隔膜電解セル
を用いた電解反応装置を用い、アセトニトリルを含む水
溶液を溶媒とし陽極酸化することにより行われる。Means for Solving the Problems The inventors of the present invention have found that the anodic oxidation of 1-hydroxy-2-naphthoic acid aryl ester can provide the 1,4-dihydroxy-2-naphthoic acid aryl ester in one step. Was found. That is, the present invention is a method for producing an aryl ester of 1,4-dihydroxy-2-naphthoic acid, which comprises anodizing an aryl ester of 1-hydroxy-2-naphthoic acid in an aqueous organic solvent. This is carried out by anodizing using an aqueous solution containing acetonitrile as a solvent using an electrolytic reaction device using a diaphragm electrolysis cell.
【０００５】本発明は上記の構成からなり、本発明の目
的化合物である１，４−ジヒドロキシ−２−ナフトエ酸
アリールエステルのアリールエステル残基のアリール部
分としては、例えば、フェニル、ナフチルなどが挙げら
れる。これらの基は置換基を有していてもよく、置換基
としては、例えば、ｔ−ブチル基等の第３級アルキル
基、ハロゲン基（例えば、クロロ、ブロモ、フルオロ
等）、ニトロ基、エステル基、シアノ基などが例示され
る。本発明の出発原料である１−ヒドロキシ−２−ナフ
トエ酸アリールエステルは公知化合物である。The present invention has the above constitution, and the aryl moiety of the aryl ester residue of the 1,4-dihydroxy-2-naphthoic acid aryl ester which is the object compound of the present invention includes, for example, phenyl, naphthyl and the like. Can be These groups may have a substituent, for example, a tertiary alkyl group such as a t-butyl group, a halogen group (eg, chloro, bromo, fluoro, etc.), a nitro group, an ester And a cyano group. The 1-hydroxy-2-naphthoic acid aryl ester which is a starting material of the present invention is a known compound.
【０００６】本発明に用いられる水性有機溶媒として
は、水と混合し得る有機溶媒（例えば、アセトニトリ
ル、メタノール、イソプロパノール、ｔ−ブタノール、
Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセ
トアミド、テトラヒドロフラン、ジオキサン、アセト
ン、メチルエチルケトン等）と水との混合溶媒が用いら
れる。当該有機溶媒と水との混合比は、出発原料である
１−ヒドロキシ−２−ナフトエ酸アリールエステルを溶
解できる範囲で、有機溶媒の種類などに応じて適宜調整
することができ、通常、有機溶媒を５０〜９５重量％程
度含有する溶媒が用いられる。特に好ましい水性有機溶
媒は、アセトニトリルを５０％以上を含む水溶液であ
り、１−ヒドロキシ−２−ナフトエ酸アリールエステル
をよく溶解する９０〜９５重量％の範囲が、選択性が高
く且つ反応が速やかに進行するので好適である。The aqueous organic solvent used in the present invention includes an organic solvent that can be mixed with water (for example, acetonitrile, methanol, isopropanol, t-butanol,
A mixed solvent of N, N-dimethylformamide, N, N-dimethylacetamide, tetrahydrofuran, dioxane, acetone, methyl ethyl ketone) and water is used. The mixing ratio of the organic solvent and water can be appropriately adjusted depending on the type of the organic solvent and the like within a range in which the starting material, 1-hydroxy-2-naphthoic acid aryl ester, can be dissolved. Is used in an amount of about 50 to 95% by weight. A particularly preferred aqueous organic solvent is an aqueous solution containing 50% or more of acetonitrile, and the range of 90 to 95% by weight in which the 1-hydroxy-2-naphthoic acid aryl ester is well dissolved has high selectivity and prompt reaction. It is preferred because it proceeds.
【０００７】電極材料としては、一般に用いられている
ものの何れも使用できるが、陽極には、例えば、炭素、
グラッシーカーボン、白金又は白金メッキ電極などが用
いられ、特に炭素が優れている。また、陰極としては、
例えば、炭素、グラッシーカーボン、銅、亜鉛などの多
くの金属版が使用でき、特に炭素が優れている。As the electrode material, any of the commonly used materials can be used.
Glassy carbon, platinum or a platinum-plated electrode is used, and carbon is particularly excellent. Also, as the cathode,
For example, many metal plates such as carbon, glassy carbon, copper, and zinc can be used, and carbon is particularly excellent.
【０００８】反応は、慣用の電極酸化法に準じて行うこ
とができるが、隔膜を使用した場合、選択性の低下が認
められることがあるので、一般的に無隔膜電解セル中で
行うのが好ましい。反応温度については、反応速度ある
いは反応の抑制を考慮すると、０〜８０℃が望ましく、
より好ましいのは２０〜６０℃である。通電量として
は、２Ｆ／モル〜１０Ｆ／モル程度が望ましく、長時間
反応を続けると副生物が生成することも考慮すると４Ｆ
／モルから８Ｆ／モル程度が望ましい。反応は通常定電
流電解法を用いて行われ、電流密度としては０．１〜
５．０Ａ／ｄｍ2程度、好ましくは１．０〜２．０Ａ／
ｄｍ2程度とされる。反応に際して、反応系には支持電
解質が添加され、支持電解質としては、例えば、硫酸、
ｐ−トルエンスルホン酸、塩化アンモニウム、塩化カリ
ウム、塩化ナトリウム等が用いられる。支持電解質の添
加量は、水性有機溶媒中の有機溶媒含量などに応じて適
宜調整されるが、通常、水性有機溶媒に対して０．１重
量％〜５重量％程度、好ましくは０．５重量％〜２重量
％程度とされる。[0008] The reaction can be carried out according to a conventional electrode oxidation method. However, when a diaphragm is used, the selectivity may be reduced. Therefore, the reaction is generally carried out in a diaphragm-free electrolytic cell. preferable. The reaction temperature is preferably 0 to 80 ° C. in consideration of the reaction rate or the suppression of the reaction,
More preferably, it is 20 to 60 ° C. The amount of electricity is preferably about 2 F / mol to 10 F / mol, and considering that by-products are generated when the reaction is continued for a long time, 4 F / mol is considered.
/ Mol to about 8 F / mol is desirable. The reaction is usually performed using a galvanostatic method, and the current density is 0.1 to
About 5.0 A / dm 2 , preferably 1.0 to 2.0 A /
dm 2 . During the reaction, a supporting electrolyte is added to the reaction system. As the supporting electrolyte, for example, sulfuric acid,
p-Toluenesulfonic acid, ammonium chloride, potassium chloride, sodium chloride and the like are used. The amount of the supporting electrolyte to be added is appropriately adjusted depending on the content of the organic solvent in the aqueous organic solvent, but is usually about 0.1% to 5% by weight, preferably 0.5% by weight based on the aqueous organic solvent. % To about 2% by weight.
【０００９】[0009]
【発明の効果】本発明によれば、１−ヒドロキシ−２−
ナフトエ酸アリールエステルから一工程かつ高収率で
１，４−ジヒドロキシ−２−ナフトエ酸アリールエステ
ルが製造できる。また、電解反応を用いるため、無公害
であり、操作が容易な上、工程的に繁雑さがなく副生物
も少なく、工業的に極めて優れた製造方法である。According to the present invention, 1-hydroxy-2-
1,4-Dihydroxy-2-naphthoic acid aryl ester can be produced from the naphthoic acid aryl ester in one step and in a high yield. In addition, since the electrolytic reaction is used, the method is pollution-free, easy to operate, has no complicated processes, has few by-products, and is an industrially excellent production method.
【００１０】[0010]
【実施例】以下、実施例により本発明を詳細に説明する
が、本発明は実施例に限定されるものではない。 実施例１ 容量１００ｍｌのビーカー型無隔膜電解セル内に陽極、
陰極とも炭素棒を用い、この電解セル内にアセトニトリ
ル７６ｇ、水４ｇ、１−ヒドロキシ−２−ナフトエ酸フ
ェニルエステル５．２９ｇ（２０ｍｍｏｌ）、支持電解
質として硫酸１ｇを加え、マグネチックスターラーによ
り溶液を撹拌しながら電流密度１．８２Ａ／ｄｍ2、反
応温度２５℃で６Ｆ／モルの通電を行った。反応後、水
２００ｍｌに排出しエーテルで抽出し溶媒留去後、固体
結晶を得た。この固体物質をカラムクロマトグラフィー
にて精製し、１，４−ジヒドロキシ−２−ナフトエ酸フ
ェニルエステルを２．１９ｇ（収率３９．０モル％）得
た。EXAMPLES The present invention will be described in detail below with reference to examples, but the present invention is not limited to the examples. Example 1 An anode was placed in a beaker-type diaphragm-free electrolytic cell having a capacity of 100 ml.
Using a carbon rod as the cathode, 76 g of acetonitrile, 4 g of water, 5.29 g (20 mmol) of 1-hydroxy-2-naphthoic acid phenyl ester and 1 g of sulfuric acid as a supporting electrolyte were added to the electrolytic cell, and the solution was stirred with a magnetic stirrer. While the current was flowing, a current density of 1.82 A / dm 2 , a reaction temperature of 25 ° C., and a current of 6 F / mol were applied. After the reaction, the mixture was discharged into 200 ml of water, extracted with ether, and the solvent was distilled off to obtain solid crystals. The solid substance was purified by column chromatography to obtain 2.19 g (yield: 39.0 mol%) of 1,4-dihydroxy-2-naphthoic acid phenyl ester.
【００１１】実施例２ 容量１００ｍｌのビーカー型無隔膜電解セル内に陽極、
陰極とも炭素棒を用い、この電解セル内にアセトニトリ
ル７６ｇ、水４ｇ、１−ヒドロキシ−２−ナフトエ酸フ
ェニルエステル５．２９ｇ（２０ｍｍｏｌ）、支持電解
質としてｐ−トルエンスルホン酸１ｇを加え、実施例１
記載の方法に従い反応を行った。その結果、１，４−ジ
ヒドロキシ−２−ナフトエ酸フェニルエステルを１．６
２ｇ（収率２８．８モル％）得た。Example 2 An anode was placed in a beaker-type diaphragm-free electrolytic cell having a capacity of 100 ml.
Using a carbon rod as the cathode, 76 g of acetonitrile, 4 g of water, 5.29 g (20 mmol) of 1-hydroxy-2-naphthoic acid phenyl ester and 1 g of p-toluenesulfonic acid as a supporting electrolyte were added to the electrolytic cell.
The reaction was performed according to the method described. As a result, 1,4-dihydroxy-2-naphthoic acid phenyl ester was converted to 1.6.
2 g (yield 28.8 mol%) was obtained.
【００１２】実施例３ 容量１００ｍｌのビーカー型無隔膜電解セル内に陽極に
は白金、陰極には炭素棒を用い、実施例１記載の方法に
従い反応を行った。その結果、１，４−ジヒドロキシ−
２−ナフトエ酸フェニルエステルを０．４４ｇ（収率
７．９モル％）得た。Example 3 A reaction was carried out according to the method described in Example 1 using platinum as an anode and a carbon rod as a cathode in a beaker-type non-diaphragm electrolytic cell having a capacity of 100 ml. As a result, 1,4-dihydroxy-
0.44 g (yield 7.9 mol%) of 2-naphthoic acid phenyl ester was obtained.
【００１３】実施例４ 容量１０００ｍｌのビーカー型無隔膜電解セル内に陽
極、陰極とも炭素棒を用い、この電解セル内にアセトニ
トリル５７０ｇ、水３０ｇ、１−ヒドロキシ−２−ナフ
トエ酸フェニルエステル３９．６４ｇ（０．１５ｍｏ
ｌ）、支持電解質として硫酸７．５ｇを加え、マグネチ
ックスターラーにより溶液を撹拌しながら電流密度２．
０Ａ／ｄｍ2、反応温度２５℃で６Ｆ／モルの通電を行
った。反応後、水１５００ｍｌに排出後、エーテルで抽
出し溶媒留去したところ、ほとんどが１，４−ジヒドロ
キシ−２−ナフトエ酸フェニルエステルである固体物を
２０．９ｇ（収率４９．９モル％）得た。Example 4 A carbon electrode was used for both the anode and the cathode in a beaker-type non-diaphragm electrolytic cell having a capacity of 1000 ml. In this electrolytic cell, 570 g of acetonitrile, 30 g of water, and 39.64 g of 1-hydroxy-2-naphthoic acid phenyl ester were used. (0.15mo
l), 7.5 g of sulfuric acid was added as a supporting electrolyte, and the current density was changed to 2. while stirring the solution with a magnetic stirrer.
A current of 6 F / mol was conducted at 0 A / dm 2 and a reaction temperature of 25 ° C. After the reaction, the reaction mixture was discharged into 1500 ml of water, extracted with ether, and the solvent was distilled off. As a result, 20.9 g (yield: 49.9 mol%) of a solid substance, mostly 1,4-dihydroxy-2-naphthoic acid phenyl ester, was obtained. Obtained.
【００１４】実施例５ 容量１００ｍｌのビーカー型無隔膜電解セル内に陽極、
陰極とも炭素棒を用い、反応温度６０℃で実施例１記載
の方法に従い反応を行った。その結果、１，４−ジヒド
ロキシ−２−ナフトエ酸フェニルエステルを２．４ｇ
（収率４３．５モル％）得た。Example 5 An anode was placed in a beaker-type non-diaphragm electrolytic cell having a capacity of 100 ml.
Using a carbon rod as the cathode, the reaction was carried out at a reaction temperature of 60 ° C. according to the method described in Example 1. As a result, 2.4 g of 1,4-dihydroxy-2-naphthoic acid phenyl ester was obtained.
(Yield 43.5 mol%).
【００１５】実施例６ 容量１００ｍｌのビーカー型無隔膜電解セル内に陽極、
陰極とも炭素棒を用い、この電解セル内にメタノール７
６ｇ、水４ｇ、１−ヒドロキシ−２−ナフトエ酸フェニ
ルエステル５．２９ｇ（２０ｍｍｏｌ）、支持電解質と
して硫酸１ｇを加え、実施例１記載の方法に従い反応を
行った。その結果、１，４−ジヒドロキシ−２−ナフト
エ酸フェニルエステルを０．２８ｇ（収率５．０モル
％）得た。Example 6 An anode was placed in a beaker-type diaphragm-free electrolytic cell having a capacity of 100 ml.
A carbon rod was used for the cathode, and methanol 7
6 g, water 4 g, 1-hydroxy-2-naphthoic acid phenyl ester 5.29 g (20 mmol), and 1 g of sulfuric acid as a supporting electrolyte were added, and the reaction was carried out according to the method described in Example 1. As a result, 0.28 g (yield 5.0 mol%) of 1,4-dihydroxy-2-naphthoic acid phenyl ester was obtained.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 西川 寛 和歌山市宇須４丁目４番６号 スガイ化 学工業株式会社内 (72)発明者 芝本 信頼 和歌山市宇須４丁目４番６号 スガイ化 学工業株式会社内 (72)発明者 松本 良暉 和歌山市宇須４丁目４番６号 スガイ化 学工業株式会社内 (56)参考文献 特開 昭61−213386（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C25B 1/00 - 15/08 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Hiroshi Nishikawa 4-6-6 Usu, Wakayama City Inside Sugaikagaku Kogyo Co., Ltd. (72) Inventor Trust Shibamoto 4-4-6 Usu, Wakayama City Sugaikagaku Inside the Industrial Co., Ltd. (72) Inventor Yoshiki Matsumoto 4-4-6 Usu, Wakayama City Inside the Sugai Chemical Industry Co., Ltd. (56) References JP-A-61-213386 (JP, A) (58) Fields investigated (Int.Cl. 7 , DB name) C25B 1/00-15/08
Claims (4)
−ナフトエ酸アリールエステルを陽極酸化することを特
徴とする１，４−ジヒドロキシ−２−ナフトエ酸アリー
ルエステルの製造方法。1. An aqueous organic solvent comprising 1-hydroxy-2
-A method for producing 1,4-dihydroxy-2-naphthoic acid aryl ester, which comprises anodic oxidation of naphthoic acid aryl ester.
の１，４−ジヒドロキシ−２−ナフトエ酸アリールエス
テルの製造方法。2. The method for producing 1,4-dihydroxy-2-naphthoic acid aryl ester according to claim 1, wherein a diaphragm-free electrolytic cell is used.
０〜９５重量％含有する水性溶媒である請求項１又は２
記載の１，４−ジヒドロキシ−２−ナフトエ酸アリール
エステルの製造方法。3. The method according to claim 1, wherein the aqueous organic solvent is acetonitrile.
3. An aqueous solvent containing 0 to 95% by weight.
The method for producing the 1,4-dihydroxy-2-naphthoic acid aryl ester described in the above.
酸アリールエステルが、１−ヒドロキシ−２−ナフトエ
酸フェニルエステルである請求項１から３のいずれかに
記載の１，４−ジヒドロキシ−２−ナフトエ酸アリール
エステルの製造方法。4. The 1,4-dihydroxy-2-acid according to claim 1, wherein the raw material 1-hydroxy-2-naphthoic acid aryl ester is 1-hydroxy-2-naphthoic acid phenyl ester. Process for producing naphthoic acid aryl ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35872391A JP3188930B2 (en) | 1991-12-27 | 1991-12-27 | Method for producing 1,4-dihydroxy-2-naphthoic acid aryl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35872391A JP3188930B2 (en) | 1991-12-27 | 1991-12-27 | Method for producing 1,4-dihydroxy-2-naphthoic acid aryl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05179476A JPH05179476A (en) | 1993-07-20 |
| JP3188930B2 true JP3188930B2 (en) | 2001-07-16 |
Family
ID=18460784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP35872391A Expired - Fee Related JP3188930B2 (en) | 1991-12-27 | 1991-12-27 | Method for producing 1,4-dihydroxy-2-naphthoic acid aryl ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3188930B2 (en) |
-
1991
- 1991-12-27 JP JP35872391A patent/JP3188930B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05179476A (en) | 1993-07-20 |
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