JPH0352850A - Benzoic acid derivative and production thereof - Google Patents
Benzoic acid derivative and production thereofInfo
- Publication number
- JPH0352850A JPH0352850A JP1184716A JP18471689A JPH0352850A JP H0352850 A JPH0352850 A JP H0352850A JP 1184716 A JP1184716 A JP 1184716A JP 18471689 A JP18471689 A JP 18471689A JP H0352850 A JPH0352850 A JP H0352850A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- butyl
- benzoic acid
- compound
- compounds
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 title claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 24
- 150000001875 compounds Chemical class 0.000 abstract description 22
- 239000000463 material Substances 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract description 5
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 229960001755 resorcinol Drugs 0.000 abstract description 3
- 239000005711 Benzoic acid Substances 0.000 abstract description 2
- 239000002841 Lewis acid Substances 0.000 abstract description 2
- 235000010233 benzoic acid Nutrition 0.000 abstract description 2
- 150000007517 lewis acids Chemical class 0.000 abstract description 2
- 239000011592 zinc chloride Substances 0.000 abstract description 2
- 235000005074 zinc chloride Nutrition 0.000 abstract description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 1
- 230000002194 synthesizing 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- WTFYGNVWNFVUIK-UHFFFAOYSA-N 2-(butylamino)phenol Chemical compound CCCCNC1=CC=CC=C1O WTFYGNVWNFVUIK-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- MRAIJALVPVPGJO-UHFFFAOYSA-N 2-(2-methylpropylamino)phenol Chemical compound CC(C)CNC1=CC=CC=C1O MRAIJALVPVPGJO-UHFFFAOYSA-N 0.000 description 1
- QIMRPGAQCKHRKB-UHFFFAOYSA-N 2-methylpropyl 4-methylbenzenesulfonate Chemical compound CC(C)COS(=O)(=O)C1=CC=C(C)C=C1 QIMRPGAQCKHRKB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 1
- QYJXDIUNDMRLAO-UHFFFAOYSA-N butyl 4-methylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=C(C)C=C1 QYJXDIUNDMRLAO-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- -1 fluoran compound Chemical class 0.000 description 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規な安息香酸誘導体及びその製造法に関す
る。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel benzoic acid derivative and a method for producing the same.
更に詳しくは、複写記録材料として有用なフルオラン化
合物の重要な製造原料となる安息香酸誘導体及びその製
造法に関する。More specifically, the present invention relates to benzoic acid derivatives, which are important raw materials for producing fluoran compounds useful as copying and recording materials, and methods for producing the same.
従来、無色ないし淡色の電子供与性化合物（発色性化合
物冫と有機もしくは無機の電子受容性物質（顕色剤）と
の呈色反応を利用し、圧力、執または電気などの外部エ
ネルギーの媒介により、伝達される情報を記録する方式
として、感圧記録、感熱記録および通ｉ！感熱記録など
がある。Conventionally, colorless or light-colored electron-donating compounds (color-forming compounds) and organic or inorganic electron-accepting substances (color developers) are used to create color reactions, and external energy such as pressure, pressure, or electricity is mediated. As methods for recording transmitted information, there are pressure-sensitive recording, heat-sensitive recording, and tsui! heat-sensitive recording.
これらの記録方式には、発色性化合物として、フルオラ
ン化合物が広く用いられている。In these recording methods, fluoran compounds are widely used as color-forming compounds.
フルオラン化合物の原料となる安息香酸誘導体としては
、従来、例えば、式（Ｉｌｌａ）、式（ＩＩＩ ｂ）か
の化合物が知られている。As benzoic acid derivatives that can be used as raw materials for fluoran compounds, compounds of formula (Illa) and formula (IIIb), for example, are conventionally known.
これらの安息香酸誘導体を原料として、それぞれ式（Ｉ
Ｖ ａ）および式（ＩＶ ｂ）のフルオラン化合物が製
造されている。Using these benzoic acid derivatives as raw materials, formulas (I
Fluoran compounds of the formula (IV a) and (IV b) have been prepared.
しかし、式（ＩＶａ）の化合物は、感圧記録材料として
用いるに＋１． カプセルオイルに対する溶解度が極め
て低いという欠点があり、また感熱記録材料として用い
るには、例えば、ビスフェノールＡ等の顕色剤と混合す
ると、それ自体灰色ないし黒灰色に発色し、これを紙に
塗布すると、灰色ないし黒灰色に着色（地汚れ）した紙
しか得られないという欠点があった。However, the compound of formula (IVa) has a +1. It has the disadvantage of extremely low solubility in capsule oil, and when used as a heat-sensitive recording material, for example, when mixed with a color developer such as bisphenol A, it develops a gray or black-gray color by itself, and when applied to paper. However, the disadvantage was that only paper colored gray or black-gray (background stains) could be obtained.
また（ＩＶｂ）の化合物は、感熱記録材料として用いる
には、発色する温度が高すぎるため、現在、より高速か
つ高密度に記録しようする要望に適合した充分な性能と
は言えず、より低温ですみやかに発色する発色性化合物
が強く望まれている。In addition, the compound (IVb) cannot be used as a heat-sensitive recording material because the temperature at which it develops color is too high, so it cannot currently be said to have sufficient performance to meet the demands for higher-speed and higher-density recording; A color-forming compound that quickly develops color is strongly desired.
本発明の課題は、上記の欠点を解消した感圧および感熱
等の記録材料に適した、フルオラン化合物の原料として
有用な安息香酸誘導体およびその製造方法を提供するこ
とである。An object of the present invention is to provide a benzoic acid derivative useful as a raw material for a fluoran compound, which is suitable for pressure-sensitive and heat-sensitive recording materials, and a method for producing the same, which eliminates the above-mentioned drawbacks.
本発明者らは、上述の課題を解決するために種々の化合
物を探索し、本発明に到達した。The present inventors have searched for various compounds to solve the above-mentioned problems and have arrived at the present invention.
すなわち、本発明は一般式（Ｉ）
（式中ｓ Ｒ１はｉｓｏ−ブチル基またはｓｅｃ−ブチ
ル基を示し、Ｒ，はｎ−ブチル基を示す）で表される安
息香酸誘導体．およびこの化合物を一般式（ＩＩ）（式
中、Ｒ１およびＲ，は、一般式（Ｉ）の場合に同じであ
る）で表される３−アミノフェノール誘導体と無水フタ
ル酸とを反応させて製造する方法である。That is, the present invention provides a benzoic acid derivative represented by the general formula (I) (wherein s R1 represents an iso-butyl group or a sec-butyl group, and R represents an n-butyl group). and this compound is produced by reacting a 3-aminophenol derivative represented by general formula (II) (wherein R1 and R are the same as in general formula (I)) and phthalic anhydride. This is the way to do it.
一般式（１）で表される本発明の化合物は、次式で表さ
れる化合物である。すなわち、Ｒ１がｉｓｏ−ブチル基
であり、Ｒ，がｎ−ブチル基である式（Ｖ）の化合物
およびＲ，がｓｅｃ−ブチル基であり、Ｒ，がｎ−ブチ
ル基
である式（ＶＩ）の化合物である。The compound of the present invention represented by general formula (1) is a compound represented by the following formula. That is, a compound of formula (V) in which R1 is an iso-butyl group and R, is an n-butyl group, and a compound of formula (VI) in which R is a sec-butyl group and R, is an n-butyl group. It is a compound of
これらの化合物は一般式（ＩＩ）
即ち、
（式中、Ｒ，およびＲ，は、一般式（Ｉ）の場合に同じ
である）と無水フタル酸とを無溶媒、あるいはベンゼン
、トルエン、キシレンまたはテトラクロロエチレン等の
溶媒中で反応させることにより製造することができる。These compounds have the general formula (II) (wherein R and R are the same as in the general formula (I)) and phthalic anhydride without a solvent or in benzene, toluene, xylene or It can be produced by reacting in a solvent such as tetrachlorethylene.
反応温度は、６０〜１４０℃の範囲で行うことが好まし
く、反応時間は反応温度により異なるが、数時間から数
十時間の間で行うのが好ましい。またこの反応の際、例
えば、塩化亜鉛のようなルイス酸を添加してもよい。The reaction temperature is preferably in the range of 60 to 140°C, and the reaction time varies depending on the reaction temperature, but is preferably carried out for several hours to several tens of hours. Further, during this reaction, a Lewis acid such as zinc chloride may be added.
一般式（Ｉ［）の化合物は、例えば、レゾルシンとｎ−
プチルアミンとより得られる３−Ｎ−ｎ−ブチルアミノ
フェノールを、例えば、イソブチルクロライド、イソブ
チルブロマイド、あるいはイソブチルトシレートのよう
なイソブチル化剤でイソブチル化を行うことにより製造
できる。また、例えば、レゾルシンとイソブチルアミン
とより得られる、３−Ｎ−イソブチルアミノフェノール
を、例えば、０プチルクロライド、ｎ−ブチルブロマイ
ドまたはローブチルトシレートのようなｎ−ブチル化剤
でｎ−ブチル化を行うことによっても得ることかできる
。The compound of general formula (I[) is, for example, resorcinol and n-
For example, 3-N-n-butylaminophenol obtained from butylamine can be produced by isobutylating with an isobutylating agent such as isobutyl chloride, isobutyl bromide, or isobutyl tosylate. Also, 3-N-isobutylaminophenol, obtained for example from resorcin and isobutylamine, can be n-butylated with an n-butylating agent such as 0-butyl chloride, n-butyl bromide or lobetyl tosylate. You can also get it by doing .
本発明の化合物は、記録材料用の発色性物質として新規
なフルオラン化合物を製造する原料として非常に有用で
ある。The compounds of the present invention are very useful as raw materials for producing novel fluoran compounds as color-forming substances for recording materials.
本発明の化合物を用いて製造されるフルオラン化合物、
例えば、つぎの式（Ｖ）の化合物は感圧記録材料に使用
する際、
カプセルオイルに
対する溶解度が極めて高く、かつ感熱記録材料に使用す
ると、地汚れのない白色度の高い紙が得られ、式（ＩＶ
ａ）や（ＩＶｂ）のフルオラン化合物に比較してより低
温ですみやかに黒色に発色するという、優れた特徴を有
している。Fluoran compounds produced using the compounds of the present invention,
For example, when the compound of formula (V) below is used in a pressure-sensitive recording material, it has extremely high solubility in capsule oil, and when used in a heat-sensitive recording material, paper with high whiteness without background stains is obtained, and the compound of the formula (IV
It has an excellent feature that it quickly develops a black color at a lower temperature than the fluoran compounds a) and (IVb).
以下、実施例により、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.
実施例工
３−Ｎ−イソブチルアミノフェノールとｎ−プチルトシ
レートより製造した３〜Ｎ−イソブチルーＮ−ｎ−プチ
ルアミノフェノール５８ｇ（ｏ． １６ａ＋ｏｌ）と無
水フタル酸５５ｇ（０． ３７ｍｏｌ）とを１００κの
１・ルエン中、４時間加熱後、反応液を温水（２００
Ｊ）で２回洗浄後、トルエン層を分離し、トルエンを留
去した。残清に２００ ｍ／のイソブＯパノールを加え
た後、５０％ＮａＯ｝１水（ｌＯｏｉ ）を加ｔ析出し
たナトリウム塩を濾過し、イソブロパノール（２００κ
）で洗浄した。ナトリウム塩を水５００κに分散後、濃
塩酸でｐＨ５〜６とした後、結晶を濾過、水洗、乾燥を
行い、５３ｇ（収率５５％）の淡いクリーム色の結晶と
して、２−（２’−ヒドロキシ−４′一Ｎ−イソブチル
ーＮ−ｎ−プチルアミノベンゾイル）安息香酸を得た。Example 3 - 58 g (o. 16a + ol) of 3-N-isobutylaminophenol produced from N-isobutylaminophenol and n-butylaminophenol and n-butylaminophenol and 55 g (0.37 mol) of phthalic anhydride were added to 100k 1. After heating for 4 hours in toluene, the reaction solution was soaked in warm water (200
After washing twice with J), the toluene layer was separated and the toluene was distilled off. After adding 200 m/l of isopropanol to the residual liquid, 50% NaO}1 water (lOoi) was added, the precipitated sodium salt was filtered, and isopropanol (200 k) was added.
). After dispersing the sodium salt in 500 k of water and adjusting the pH to 5-6 with concentrated hydrochloric acid, the crystals were filtered, washed with water, and dried to give 53 g (yield 55%) of pale cream-colored crystals as 2-(2'- Hydroxy-4'-N-isobutyl-N-n-butylaminobenzoyl)benzoic acid was obtained.
収率５５％。融点１６０５〜１６４℃
実施例２
３−Ｎ−ｓｅｃ−ブチルアミノフェノールとｎ−プチル
トシレートより製造した３−Ｎ−ｎ−ブチルーＮ−ｓｅ
ｃ−プチルアミノフェノール５８ｇ（０． １ ６ｍｏ
ｌ ）と無水フタル酸５５ｇ（０． ３７ｍｏｌ）と
を１００ ｉのトルエン中、１５時間加熱後、反応液を
厘水（２００ｒｒｌ）で２回洗浄後、トルエン層を分離
し、トルエンを留去した。Yield 55%. Melting point 1605-164°C Example 2 3-N-n-butyl-N-se produced from 3-N-sec-butylaminophenol and n-butyl tosylate
c-butylaminophenol 58g (0.16mo
After heating 55 g (0.37 mol) of phthalic anhydride in 100 i of toluene for 15 hours, the reaction solution was washed twice with diluted water (200 rrl), the toluene layer was separated, and the toluene was distilled off. .
残渣にイソプロパノール２００ｄと４０％ＮａＯＨ水溶
液を加え３０分間室温で放置後、析出したナトリウム塩
を濾過し、イソプロパノール（２００ｒｎｌ）で洗浄し
た。200 d of isopropanol and a 40% aqueous NaOH solution were added to the residue, and the mixture was allowed to stand at room temperature for 30 minutes, and the precipitated sodium salt was filtered and washed with isopropanol (200 rnl).
ナトリウム垣を水４００ ＋Ｊに分散後、１０％ＨＣｆ
にてｐＨ６とした後、析出した固体を集め、水洗、乾燥
し、目的とする安息香酸誘導体２−（４’ 一Ｎ−ｎ−
ブチルーＮ−ｓｅｃ−プチルアミノー２′〜ヒドロキノ
ベンゾイル安患香酸を、
５３ｇ（収率５５％）の淡いクリーム色の結晶として得
た。After dispersing the sodium fence in 400 + J of water, 10% HCf
The precipitated solid was collected, washed with water, and dried to obtain the desired benzoic acid derivative 2-(4'
Butyl-N-sec-butylamino-2'-hydroquinobenzoylbenzoic acid was obtained as pale cream-colored crystals of 53 g (yield 55%).
融点 １５８．５〜１６０ ℃melting point 158.5-160℃
Claims (2)
ル基を示し、Ｒ＿２はｎ−ブチル基を示す）。(1) Benzoic acid derivative represented by general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R_1 represents an iso-butyl group or a sec-butyl group, and R_2 represents an n-butyl group).
ル基を示し、Ｒ＿２はｎ−ブチル基を示す）で表される
３−アミノフェノール誘導体と、無水フタル酸とを反応
させることを特徴とする請求項（１）記載の一般式（
I ）で表される安息香酸誘導体の製造方法。(2) General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (In the formula, R_1 represents an iso-butyl group or a sec-butyl group, and R_2 represents an n-butyl group.) The general formula (1) according to claim (1), characterized in that the 3-aminophenol derivative represented by
A method for producing a benzoic acid derivative represented by I).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1184716A JPH0352850A (en) | 1989-07-19 | 1989-07-19 | Benzoic acid derivative and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1184716A JPH0352850A (en) | 1989-07-19 | 1989-07-19 | Benzoic acid derivative and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0352850A true JPH0352850A (en) | 1991-03-07 |
Family
ID=16158116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1184716A Pending JPH0352850A (en) | 1989-07-19 | 1989-07-19 | Benzoic acid derivative and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0352850A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0853079A1 (en) * | 1997-01-09 | 1998-07-15 | Ciba SC Holding AG | Production of keto acids |
-
1989
- 1989-07-19 JP JP1184716A patent/JPH0352850A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0853079A1 (en) * | 1997-01-09 | 1998-07-15 | Ciba SC Holding AG | Production of keto acids |
| CN100357258C (en) * | 1997-01-09 | 2007-12-26 | 希巴特殊化学控股公司 | Production of keto acids |
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