JPH0216753B2 - - Google Patents
Info
- Publication number
- JPH0216753B2 JPH0216753B2 JP11780083A JP11780083A JPH0216753B2 JP H0216753 B2 JPH0216753 B2 JP H0216753B2 JP 11780083 A JP11780083 A JP 11780083A JP 11780083 A JP11780083 A JP 11780083A JP H0216753 B2 JPH0216753 B2 JP H0216753B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- carboxylic acid
- yield
- formula
- reaction
- 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
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 10
- QQVIOEXFJFFVID-UHFFFAOYSA-N 3-acetylthiophene-2-carboxylic acid Chemical compound CC(=O)C=1C=CSC=1C(O)=O QQVIOEXFJFFVID-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- LIKIMWYKJUFVJP-UHFFFAOYSA-N 5-acetylthiophene-2-carboxylic acid Chemical compound CC(=O)C1=CC=C(C(O)=O)S1 LIKIMWYKJUFVJP-UHFFFAOYSA-N 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 10
- 150000004702 methyl esters Chemical class 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- SBXFKIGPJZKIRO-UHFFFAOYSA-N 5-(2-bromoacetyl)thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(C(=O)CBr)S1 SBXFKIGPJZKIRO-UHFFFAOYSA-N 0.000 description 5
- -1 aliphatic alcohols Chemical class 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- NRKPNQIAEYLXNZ-UHFFFAOYSA-N 5-(2,2-dibromoacetyl)thiophene-2-carboxylic acid Chemical compound BrC(C(=O)C1=CC=C(S1)C(=O)O)Br NRKPNQIAEYLXNZ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 1
- XYGMOSFVNZUTEK-UHFFFAOYSA-N 4-acetylthiophene-2-carboxylic acid Chemical compound CC(=O)C1=CSC(C(O)=O)=C1 XYGMOSFVNZUTEK-UHFFFAOYSA-N 0.000 description 1
- ODEHUFLHQIKJNG-UHFFFAOYSA-N 5-(2-bromoacetyl)thiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC(C(=O)CBr)=C1 ODEHUFLHQIKJNG-UHFFFAOYSA-N 0.000 description 1
- BDYPBGQJEQRZDL-UHFFFAOYSA-N 5-(2-chloroacetyl)thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(C(=O)CCl)S1 BDYPBGQJEQRZDL-UHFFFAOYSA-N 0.000 description 1
- GSPVECVNXXJOGI-UHFFFAOYSA-N 5-acetylthiophene-3-carboxylic acid Chemical compound CC(=O)C1=CC(C(O)=O)=CS1 GSPVECVNXXJOGI-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11780083A JPS608288A (ja) | 1983-06-28 | 1983-06-28 | モノハロアセチルチオフエンカルボン酸およびそのエステルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11780083A JPS608288A (ja) | 1983-06-28 | 1983-06-28 | モノハロアセチルチオフエンカルボン酸およびそのエステルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS608288A JPS608288A (ja) | 1985-01-17 |
| JPH0216753B2 true JPH0216753B2 (en, 2012) | 1990-04-18 |
Family
ID=14720590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11780083A Granted JPS608288A (ja) | 1983-06-28 | 1983-06-28 | モノハロアセチルチオフエンカルボン酸およびそのエステルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS608288A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61152677A (ja) * | 1984-12-26 | 1986-07-11 | Seitetsu Kagaku Co Ltd | ２−ハロアセチルチオフエン類の製造法 |
| JP2549018B2 (ja) * | 1990-12-17 | 1996-10-30 | 新日本製鐵株式会社 | 耐熱性および耐食性に優れたフェライト系ステンレス鋼熱延鋼帯の製造方法 |
-
1983
- 1983-06-28 JP JP11780083A patent/JPS608288A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS608288A (ja) | 1985-01-17 |
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