JPS623830B2 - - Google Patents
Info
- Publication number
- JPS623830B2 JPS623830B2 JP54090314A JP9031479A JPS623830B2 JP S623830 B2 JPS623830 B2 JP S623830B2 JP 54090314 A JP54090314 A JP 54090314A JP 9031479 A JP9031479 A JP 9031479A JP S623830 B2 JPS623830 B2 JP S623830B2
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- acid
- ester
- formula
- alkyl group
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- -1 2-methoxy-5-chloroterephthalic acid-4-methyl ester Chemical compound 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- OXUBUSSEVOLEPD-UHFFFAOYSA-N methyl 2-chloro-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1Cl OXUBUSSEVOLEPD-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- AQHFCRYZABKUEV-UHFFFAOYSA-N 2-chloro-5-methoxybenzoic acid Chemical compound COC1=CC=C(Cl)C(C(O)=O)=C1 AQHFCRYZABKUEV-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- JSTRUXOUUMYPCN-UHFFFAOYSA-N dimethyl 2-chloro-5-methoxybenzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC(OC)=C(C(=O)OC)C=C1Cl JSTRUXOUUMYPCN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、新規なテレフタル酸誘導体およびそ
の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel terephthalic acid derivative and a method for producing the same.
本発明の新規なテレフタル酸は、一般式
（式中、Ｒは低級アルキル基、Ｘはハロゲンを表
わす。）
で示される２−メトキシ−５−ハロテレフタル酸
−４−アルキルエステルである。 The novel terephthalic acid of the present invention has the general formula (In the formula, R represents a lower alkyl group and X represents a halogen.) It is a 2-methoxy-5-haloterephthalic acid-4-alkyl ester represented by the following formula.
この化合物は医薬品製造の中間物質として極め
て有用である。たとえば、この化合物の１位のカ
ルボキシル基を酸クロリドとなし、次いで非対称
ジアミン、たとえばＮ・Ｎ−ジエチルエチレンジ
アミン等を作用させ、最後に４位のカルボン酸エ
ステルをヒドロキシルアミンを用いてアミノ基に
変換させることにより得られる２−メトキシ−４
−アミノ−５−クロロ−Ｎ−（第３アミノエチ
ル）ベンツアミドは、鎮痛、鎮静、神経弛緩、精
神緊張低下等に薬理作用を呈する有用な医薬品で
ある。 This compound is extremely useful as an intermediate in pharmaceutical manufacturing. For example, the carboxyl group at the 1st position of this compound is converted into an acid chloride, then an asymmetric diamine such as N·N-diethylethylenediamine is reacted with, and finally the carboxylic acid ester at the 4th position is converted to an amino group using hydroxylamine. 2-methoxy-4 obtained by
-Amino-5-chloro-N-(tertiary aminoethyl)benzamide is a useful drug that exhibits pharmacological effects such as analgesia, sedation, nerve relaxation, and decreased mental tone.
上記一般式において、Ｒで表わされる低級アル
キル基としては、C1〜４のアルキル基が好まし
く、具体的には、メチル基、エチル基、プロピル
基、イソプロピル基、ブチル基、イソブチル基等
が挙げられる。また、Ｘで表わされるハロゲンと
しては、フツ素、塩素、臭素等が挙げられ、特に
塩素が好ましい。 In the above general formula, the lower alkyl group represented by R is preferably a C1-4 alkyl group, and specific examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, etc. . Further, examples of the halogen represented by X include fluorine, chlorine, bromine, etc., and chlorine is particularly preferred.
本発明の新規なテレフタル酸誘導体のうち、特
に好ましいものは、２−メトキシ−５−クロロテ
レフタル酸−４−メチルエステルおよび２−メト
キシ−５−クロロテレフタル酸−４−エチルエス
テルである。 Among the novel terephthalic acid derivatives of the present invention, particularly preferred are 2-methoxy-5-chloroterephthalic acid-4-methyl ester and 2-methoxy-5-chloroterephthalic acid-4-ethyl ester.
本発明のもう一つの発明は、一般式
（式中、R′はアルキル基、ＲおよびＸは前記と同
じ意味を表わす。）
で示される２−メトキシ−５−ハロテレフタル酸
−１・４−ジアルキルエステルを、塩基の存在下
で１位のカルボン酸エステルを選択的に加水分解
することを特徴とする一般式
（式中、ＲおよびＸは前記と同じ意味を表わす。）
で示される新規化合物２−メトキシ−５−ハロテ
レフタル酸−４−アルキルエステルの製造法であ
る。 Another invention of the present invention is the general formula (In the formula, R' is an alkyl group, and R and A general formula characterized by selectively hydrolyzing the carboxylic acid ester of (In the formula, R and X have the same meanings as above.) This is a method for producing a novel compound 2-methoxy-5-haloterephthalic acid 4-alkyl ester represented by the following formula.
この製法の具体的な一例を説明すると次のとお
りである。 A specific example of this manufacturing method will be explained as follows.
すなわち、原料物質２−メトキシ−５−ハロテ
レフタル酸−１・４−ジアルキルエステルを水ま
たは低級アルコールを溶媒とし、好ましくは低級
アルコール中で、適当な塩基、たとえば、水酸化
ナトリウム、水酸化カリウム等の無機塩基類、ま
たはピリジン、ピコリン、トリエチルアミン等の
有機塩基類を、原料物質に対して当モルないし10
倍モル、好ましくは当モルないし５倍モル加え、
室温ないし150℃、好ましくは室温ないし溶媒の
加熱還流下、１ないし10時間、好ましくは１ない
し５時間エステル加水分解を行なうことにより、
目的物質である２−メトキシ−５−ハロテレフタ
ル酸−４−アルキルエステルを得ることができ
る。 That is, the raw material 2-methoxy-5-haloterephthalic acid-1,4-dialkyl ester is mixed with water or a lower alcohol as a solvent, preferably in a lower alcohol, with a suitable base such as sodium hydroxide, potassium hydroxide, etc. of inorganic bases or organic bases such as pyridine, picoline, triethylamine, etc., in an amount of equivalent mole to 10 molar based on the raw material.
Add twice the mole, preferably equimolar to 5 times the mole,
By carrying out ester hydrolysis at room temperature to 150°C, preferably at room temperature to refluxing the solvent for 1 to 10 hours, preferably 1 to 5 hours,
The target substance, 2-methoxy-5-haloterephthalic acid-4-alkyl ester, can be obtained.
以下、実施例を挙げて説明するが、本発明は、
これらに限定されるものではない。 The present invention will be described below with reference to Examples.
It is not limited to these.
実施例 １
２−メトキシ−５−クロロテレフタル酸−４−
メチルエステルの製造：
２−メトキシ−５−クロロテレフタル酸−１・
４−ジメチルエステル5.1ｇをメタノール20c.c.に
溶解した溶液に、水酸化カリウム1.6ｇを20c.c.に
溶解した溶液を滴下する。滴下後２時間室温で放
置すると反応が終了する。得られた反応液を減圧
下メタノールを留去すると、白色結晶が析出す
る。この結晶を水100c.c.に溶解し、水に不溶なも
のを取すると、原料である２−メトキシ−５−
クロロテレフタル酸−１・４−ジメチルエステル
1.0ｇが回収される。液を５％塩酸で酸性化す
ると、白色結晶が得られるので、一夜５℃で放置
後取すると、目的とする２−メトキシ−５−ク
ロロテレフタル酸−４−メチルエステルの結晶
（融点133℃）が3.8ｇ得られた。Example 1 2-methoxy-5-chloroterephthalic acid-4-
Production of methyl ester: 2-methoxy-5-chloroterephthalic acid-1.
A solution of 1.6 g of potassium hydroxide dissolved in 20 c.c. is added dropwise to a solution of 5.1 g of 4-dimethyl ester dissolved in 20 c.c. of methanol. After the dropwise addition, the reaction is completed by standing at room temperature for 2 hours. When methanol is distilled off from the resulting reaction solution under reduced pressure, white crystals are precipitated. Dissolve these crystals in 100 c.c. of water and remove the water-insoluble crystals.The raw material, 2-methoxy-5-
Chloroterephthalic acid-1,4-dimethyl ester
1.0g is recovered. When the liquid is acidified with 5% hydrochloric acid, white crystals are obtained. After standing at 5°C overnight, the desired crystals of 2-methoxy-5-chloroterephthalic acid-4-methyl ester (melting point 133°C) are obtained. 3.8g of was obtained.
IRスペクトル
3000cm-1〜2000cm-1 −COOH
1730cm-1 −COOCH3
1700cm-1 −COOH由来の＞Ｃ＝０
元素分析値 C10H9ClO5として
理論値 C49.10；H3.68；Cl 14.49
実験値 C49.00；H3.61；Cl 14.40
実施例 ２
２−クロロ−５−メトキシ安息香酸メチルエス
テルの製造：
実施例１で得た２−メトキシ−５−クロロテレ
フタル酸−４−メチルエステル0.12ｇを水200c.c.
に溶解後、酢酸バリウム0.25ｇを含む水溶液50c.c.
を加え、20〜25℃にて１時間撹拌する。得られた
反応液を減圧下蒸発させると、白色粉末0.34ｇを
得る。この白色粉末を170℃に加熱した電気炉に
て１時間加熱すると、加熱の初期において激しく
発泡を伴い、脱炭酸反応が起り、黒かつ色の粉末
となる。この粉末を水にデスラリーした後、１規
定塩酸で中和し、酢酸エチル100c.c.で抽出する。
得られた酢酸エチル層から２−クロロ−５−メト
キシ安息香酸メチルエステルが白色結晶として得
られた。IR spectrum 3000cm -1 〜2000cm -1 −COOH 1730cm −1 −COOCH 3 1700cm −1 >C=0 derived from −COOH Elemental analysis value C 10 H 9 ClO 5 Theoretical value C49.10; H3.68; Cl 14.49 Experimental value C49.00; H3.61; Cl 14.40 Example 2 Production of 2-chloro-5-methoxybenzoic acid methyl ester: 2-methoxy-5-chloroterephthalic acid-4-methyl ester obtained in Example 1 0.12 g to 200 c.c. of water.
After dissolving in 50 c.c. of an aqueous solution containing 0.25 g of barium acetate.
and stir at 20-25°C for 1 hour. The resulting reaction solution is evaporated under reduced pressure to obtain 0.34 g of white powder. When this white powder is heated for 1 hour in an electric furnace heated to 170°C, it foams violently in the initial stage of heating, and a decarboxylation reaction occurs, resulting in a black colored powder. This powder was deslurried in water, neutralized with 1N hydrochloric acid, and extracted with 100 c.c. of ethyl acetate.
2-chloro-5-methoxybenzoic acid methyl ester was obtained as white crystals from the obtained ethyl acetate layer.
元素分析値 C9H9ClO3として
理論値 C53.88；H4.52；Cl 17.67
実験値 C53.01；H4.48；Cl 16.95
本実施例で得られた２−クロロ−５−メトキシ
安息香酸メチルエステルは、上述元素分析をはじ
め、IR、NMR分析で標品と完全に一致した。し
たがつて、本実施例より実施例１で得られた化合
物は、２−メトキシ−５−クロロテレフタル酸−
４−メチルエステルであることが裏づけられた。Elemental analysis value C 9 H 9 ClO 3 Theoretical value C53.88; H4.52; Cl 17.67 Experimental value C53.01; H4.48; Cl 16.95 2-chloro-5-methoxybenzoic acid obtained in this example The methyl ester completely matched the standard in the elemental analysis mentioned above, as well as in IR and NMR analyses. Therefore, the compound obtained in Example 1 from this example is 2-methoxy-5-chloroterephthalic acid-
It was confirmed that it was 4-methyl ester.
実施例 ３
２−メトキシ−５−クロロテレフタル酸−４−
メチルエステルの製造：
２−メトキシ−５−クロロテレフタル酸−１・
４−ジメチルエステル2.6ｇをメタノール20c.c.に
溶解し、ピリジン4.1c.c.および水0.9c.c.を加え、耐
圧オートクーブに仕込む。反応温度150℃で５時
間反応後、反応液を取り出し、溶媒を減圧下留去
する。以下、実施例１と同様な処理を行つて、２
−メトキシ−５−クロロテレフタル酸−４−メチ
ルエステル2.0ｇを得た。Example 3 2-methoxy-5-chloroterephthalic acid-4-
Production of methyl ester: 2-methoxy-5-chloroterephthalic acid-1.
Dissolve 2.6 g of 4-dimethyl ester in 20 c.c. of methanol, add 4.1 cc of pyridine and 0.9 cc of water, and place in a pressure-resistant autocube. After reacting for 5 hours at a reaction temperature of 150°C, the reaction solution was taken out and the solvent was distilled off under reduced pressure. Hereinafter, by performing the same process as in Example 1, 2
2.0 g of -methoxy-5-chloroterephthalic acid-4-methyl ester was obtained.
実施例 ４
２−メトキシ−５−クロロテレフタル酸−４−
メチルエステルの製造：
原料２−メトキシ−５−クロロテレフタル酸−
１・５−ジメチルエステル5.4ｇを用い、実施例
１と同様な操作を行ない、２−メトキシ−５−ク
ロロテレフタル酸−４−エチルエステル2.1ｇを
得た。Example 4 2-methoxy-5-chloroterephthalic acid-4-
Production of methyl ester: Raw material 2-methoxy-5-chloroterephthalic acid-
The same operation as in Example 1 was carried out using 5.4 g of 1,5-dimethyl ester to obtain 2.1 g of 2-methoxy-5-chloroterephthalic acid-4-ethyl ester.
元素分析値 C11H11ClO5として 理論値 C51.08；H4.29；Cl 13.71 実験値 C50.86；H4.15；Cl 13.08Elemental analysis value C 11 H 11 ClO 5 Theoretical value C51.08; H4.29; Cl 13.71 Experimental value C50.86; H4.15; Cl 13.08
Claims (1)
わす。） で示される新規化合物２−メトキシ−５−ハロテ
レフタル酸−４−アルキルエステル。 ２ ＲがC1〜４のアルキル基である特許請求の
範囲第１項記載の化合物。 ３ Ｘが塩素である特許請求の範囲第１項記載の
化合物。 ４ 新規化合物が２−メトキシ−５−クロロテレ
フタル酸−４−メチルエステルである特許請求の
範囲第１項記載の化合物。 ５ 新規化合物が２−メトキシ−５−クロロテレ
フタル酸−４−エチルエステルである特許請求の
範囲第１項記載の化合物。 ６ 一般式 （式中、Ｒは低級アルキル基、R′はアルキル基、
Ｘはハロゲンを表わす。） で示される２−メトキシ−５−ハロテレフタル酸
−１・４−ジアルキルエステルを、塩基の存在下
で１位のカルボン酸エステルを選択的に加水分解
することを特徴とする一般式 （式中、ＲおよびＸは前記と同じ意味を表わす。） で示される新規化合物２−メトキシ−５−ハロテ
レフタル酸−４−アルキルエステルの製造法。[Claims] 1. General formula (In the formula, R represents a lower alkyl group and X represents a halogen.) A novel compound 2-methoxy-5-haloterephthalic acid-4-alkyl ester represented by the following formula. 2. The compound according to claim 1, wherein R is a C1-4 alkyl group. 3. The compound according to claim 1, wherein X is chlorine. 4. The compound according to claim 1, wherein the new compound is 2-methoxy-5-chloroterephthalic acid-4-methyl ester. 5. The compound according to claim 1, wherein the new compound is 2-methoxy-5-chloroterephthalic acid-4-ethyl ester. 6 General formula (In the formula, R is a lower alkyl group, R' is an alkyl group,
X represents halogen. ) A general formula characterized by selectively hydrolyzing the 1-position carboxylic acid ester of 2-methoxy-5-haloterephthalic acid-1,4-dialkyl ester represented by the following in the presence of a base: (In the formula, R and X have the same meanings as above.) A method for producing a novel compound 2-methoxy-5-haloterephthalic acid 4-alkyl ester represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9031479A JPS5616445A (en) | 1979-07-18 | 1979-07-18 | Novel derivative of terephthalic acid and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9031479A JPS5616445A (en) | 1979-07-18 | 1979-07-18 | Novel derivative of terephthalic acid and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5616445A JPS5616445A (en) | 1981-02-17 |
| JPS623830B2 true JPS623830B2 (en) | 1987-01-27 |
Family
ID=13995059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9031479A Granted JPS5616445A (en) | 1979-07-18 | 1979-07-18 | Novel derivative of terephthalic acid and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5616445A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102173885B1 (en) * | 2020-03-04 | 2020-11-04 | 이원익 | Device working cold medium pipe for aircondisioner scondensers |
-
1979
- 1979-07-18 JP JP9031479A patent/JPS5616445A/en active Granted
Non-Patent Citations (1)
| Title |
|---|
| CHEM PHARM BULL * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102173885B1 (en) * | 2020-03-04 | 2020-11-04 | 이원익 | Device working cold medium pipe for aircondisioner scondensers |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5616445A (en) | 1981-02-17 |
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