CH378901A - Verfahren zur Herstellung von Thiophencarbonsäuren und deren Estern - Google Patents

Verfahren zur Herstellung von Thiophencarbonsäuren und deren Estern

Info

Publication number: CH378901A
Authority: CH; Switzerland
Prior art keywords: methyl; acid; bis; solution; water
Prior art date: 1958-04-12

Application number

CH7182959A

Other languages

German (de)

English (en)

Inventor

Fiesselmann Hans Dr Prof

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1958-04-12

Filing date

1959-04-10

Publication date

1964-06-30

1959-04-10 Application filed by Hoechst Ag filed Critical Hoechst Ag

1964-06-30 Publication of CH378901A publication Critical patent/CH378901A/de

Links

150000002148 esters Chemical class 0.000 title claims description 21
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 title claims description 10
238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 3
-1 alkyl radical Chemical class 0.000 claims description 101
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 22
239000003795 chemical substances by application Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 4
238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 186
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
239000000243 solution Substances 0.000 description 88
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 74
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 70
239000000203 mixture Substances 0.000 description 50
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 44
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
238000001816 cooling Methods 0.000 description 31
238000002844 melting Methods 0.000 description 28
230000008018 melting Effects 0.000 description 28
239000002904 solvent Substances 0.000 description 27
238000009835 boiling Methods 0.000 description 26
239000003921 oil Substances 0.000 description 26
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 25
238000006243 chemical reaction Methods 0.000 description 22
238000004821 distillation Methods 0.000 description 22
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
229910052938 sodium sulfate Inorganic materials 0.000 description 21
235000011152 sodium sulphate Nutrition 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
238000001953 recrystallisation Methods 0.000 description 19
239000002253 acid Substances 0.000 description 16
239000007788 liquid Substances 0.000 description 15
239000002244 precipitate Substances 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 12
238000001035 drying Methods 0.000 description 12
239000010410 layer Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 11
238000000746 purification Methods 0.000 description 10
239000000126 substance Substances 0.000 description 10
239000000047 product Substances 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
239000012043 crude product Substances 0.000 description 7
238000005194 fractionation Methods 0.000 description 7
PMQKYYLTCURWFB-UHFFFAOYSA-N CC(C(C(C)=O)=CSCC(OC)=O)=O Chemical compound CC(C(C(C)=O)=CSCC(OC)=O)=O PMQKYYLTCURWFB-UHFFFAOYSA-N 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000005457 ice water Substances 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
239000000155 melt Substances 0.000 description 5
NYCCIBQOXXHQBY-UHFFFAOYSA-N methyl 3-(2-methylpropyl)thiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1CC(C)C NYCCIBQOXXHQBY-UHFFFAOYSA-N 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000005406 washing Methods 0.000 description 5
RPZBMBIIOOKZMB-UHFFFAOYSA-N 3,4-dimethylthiophene-2-carboxylic acid Chemical compound CC1=CSC(C(O)=O)=C1C RPZBMBIIOOKZMB-UHFFFAOYSA-N 0.000 description 4
RNNMFMKKUDBLHJ-UHFFFAOYSA-N 4-methyl-3-phenylthiophene-2-carboxylic acid Chemical compound CC1=CSC(C(O)=O)=C1C1=CC=CC=C1 RNNMFMKKUDBLHJ-UHFFFAOYSA-N 0.000 description 4
FIFOCEFOCMXMKA-UHFFFAOYSA-N 6-ethoxyhex-5-ene-2,4-dione Chemical compound CCOC=CC(=O)CC(C)=O FIFOCEFOCMXMKA-UHFFFAOYSA-N 0.000 description 4
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
UEBMUDPQPBOBKH-UHFFFAOYSA-N methyl 2-(3-oxo-3-phenylprop-1-enyl)sulfanylacetate Chemical compound C(=O)(OC)CSC=CC(=O)C1=CC=CC=C1 UEBMUDPQPBOBKH-UHFFFAOYSA-N 0.000 description 4
WARKBOSDOBRRKH-UHFFFAOYSA-N methyl 5-methyl-3-phenylthiophene-2-carboxylate Chemical compound S1C(C)=CC(C=2C=CC=CC=2)=C1C(=O)OC WARKBOSDOBRRKH-UHFFFAOYSA-N 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
QGQBKGYXFUDGDQ-UHFFFAOYSA-N 3,5-dimethylthiophene-2-carboxylic acid Chemical compound CC1=CC(C)=C(C(O)=O)S1 QGQBKGYXFUDGDQ-UHFFFAOYSA-N 0.000 description 3
RGRSMPHTNOFHDQ-UHFFFAOYSA-N 3-ethyl-4-methylthiophene-2-carboxylic acid Chemical compound CCC=1C(C)=CSC=1C(O)=O RGRSMPHTNOFHDQ-UHFFFAOYSA-N 0.000 description 3
LTJUVCDBSMJYJF-UHFFFAOYSA-N 3-hydroxy-2-methyl-1-phenylprop-2-en-1-one Chemical compound OC=C(C)C(=O)C1=CC=CC=C1 LTJUVCDBSMJYJF-UHFFFAOYSA-N 0.000 description 3
IMHBKHIZPZRECU-UHFFFAOYSA-N 3-methoxy-1-phenylprop-2-en-1-one Chemical compound COC=CC(=O)C1=CC=CC=C1 IMHBKHIZPZRECU-UHFFFAOYSA-N 0.000 description 3
KWWGBNRBZMJKPA-UHFFFAOYSA-N 3-phenylthiophene-2-carboxylic acid Chemical compound S1C=CC(C=2C=CC=CC=2)=C1C(=O)O KWWGBNRBZMJKPA-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
150000001241 acetals Chemical class 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 3
KMRDWARKIQVJCM-UHFFFAOYSA-N methyl 3,4,5-trimethylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C)=C(C)C=1C KMRDWARKIQVJCM-UHFFFAOYSA-N 0.000 description 3
ATJHYKAQHBXBHM-UHFFFAOYSA-N methyl 3,5-dimethylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C)=CC=1C ATJHYKAQHBXBHM-UHFFFAOYSA-N 0.000 description 3
OSWPMMUUONCFSU-UHFFFAOYSA-N methyl 3-(4-methylphenyl)thiophene-2-carboxylate Chemical compound S1C=CC(C=2C=CC(C)=CC=2)=C1C(=O)OC OSWPMMUUONCFSU-UHFFFAOYSA-N 0.000 description 3
WIWLXTOACVPLHM-UHFFFAOYSA-N methyl 3-[(4-methoxyphenyl)methyl]thiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC1CC1=CC=C(C=C1)OC WIWLXTOACVPLHM-UHFFFAOYSA-N 0.000 description 3
CVHLZPYFGVJCBE-UHFFFAOYSA-N methyl 3-ethyl-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C1CC)C CVHLZPYFGVJCBE-UHFFFAOYSA-N 0.000 description 3
QEWSESNPXKZRJE-UHFFFAOYSA-N methyl 4-acetyl-3-methylthiophene-2-carboxylate Chemical compound COC(=O)C1=C(C)C(=CS1)C(C)=O QEWSESNPXKZRJE-UHFFFAOYSA-N 0.000 description 3
UVJAQLAJYQYTJP-UHFFFAOYSA-N methyl 4-methyl-3-phenylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C1C1=CC=CC=C1)C UVJAQLAJYQYTJP-UHFFFAOYSA-N 0.000 description 3
230000001376 precipitating effect Effects 0.000 description 3
230000000630 rising effect Effects 0.000 description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000000967 suction filtration Methods 0.000 description 3
150000003568 thioethers Chemical class 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
MKCAHYJUGPLWPX-UHFFFAOYSA-N 1,1-dimethoxy-5-methylhexan-3-one Chemical compound COC(OC)CC(=O)CC(C)C MKCAHYJUGPLWPX-UHFFFAOYSA-N 0.000 description 2
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 2
GCEHBBDKPSCJCF-UHFFFAOYSA-N 3-(4-methylphenyl)thiophene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=C(C(O)=O)SC=C1 GCEHBBDKPSCJCF-UHFFFAOYSA-N 0.000 description 2
BOEDZRMEKRQLOV-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methyl]thiophene-2-carboxylic acid Chemical compound COC1=CC=C(CC2=C(SC=C2)C(O)=O)C=C1 BOEDZRMEKRQLOV-UHFFFAOYSA-N 0.000 description 2
RERQKFGKHQZDHH-UHFFFAOYSA-N 3-hydroxy-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound COC1=CC=C(C(=O)C=CO)C=C1 RERQKFGKHQZDHH-UHFFFAOYSA-N 0.000 description 2
GSOHKPVFCOWKPU-UHFFFAOYSA-N 3-methylpentane-2,4-dione Chemical compound CC(=O)C(C)C(C)=O GSOHKPVFCOWKPU-UHFFFAOYSA-N 0.000 description 2
IFLKEBSJTZGCJG-UHFFFAOYSA-N 3-methylthiophene-2-carboxylic acid Chemical compound CC=1C=CSC=1C(O)=O IFLKEBSJTZGCJG-UHFFFAOYSA-N 0.000 description 2
XNKWXHNVPRFHBK-UHFFFAOYSA-N 4-acetyl-3-methylthiophene-2-carboxylic acid Chemical compound CC(=O)C1=CSC(C(O)=O)=C1C XNKWXHNVPRFHBK-UHFFFAOYSA-N 0.000 description 2
TZFDMTHFKWUKQH-UHFFFAOYSA-N 5-methyl-3-phenylthiophene-2-carboxylic acid Chemical compound C1(=CC=CC=C1)C1=C(SC(=C1)C)C(=O)O TZFDMTHFKWUKQH-UHFFFAOYSA-N 0.000 description 2
MCPKOAFMWHHPKO-UHFFFAOYSA-N C(=O)(O)CSC=C(C(C)=O)C(C)=O Chemical compound C(=O)(O)CSC=C(C(C)=O)C(C)=O MCPKOAFMWHHPKO-UHFFFAOYSA-N 0.000 description 2
MHVPRZBISZQHJP-UHFFFAOYSA-N CCOC(=O)CSC=C(C(=O)C)C(=O)C Chemical compound CCOC(=O)CSC=C(C(=O)C)C(=O)C MHVPRZBISZQHJP-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
MVYRYONHXOTEKE-UHFFFAOYSA-N methyl 3,4-dimethylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C)C=1C MVYRYONHXOTEKE-UHFFFAOYSA-N 0.000 description 2
BRWROFVPMUPMJQ-UHFFFAOYSA-N methyl 3-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1C BRWROFVPMUPMJQ-UHFFFAOYSA-N 0.000 description 2
TUSSOROTMWPECZ-UHFFFAOYSA-N methyl 3-phenylthiophene-2-carboxylate Chemical compound S1C=CC(C=2C=CC=CC=2)=C1C(=O)OC TUSSOROTMWPECZ-UHFFFAOYSA-N 0.000 description 2
229940032007 methylethyl ketone Drugs 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000011833 salt mixture Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229930192474 thiophene Natural products 0.000 description 2
VPNPSLGQCITHEP-UHFFFAOYSA-N 1,1-dimethoxybutan-2-one Chemical compound CCC(=O)C(OC)OC VPNPSLGQCITHEP-UHFFFAOYSA-N 0.000 description 1
IRNJRGVFXLVQEK-UHFFFAOYSA-N 2-methyl-1-phenylbutane-1,3-dione Chemical compound CC(=O)C(C)C(=O)C1=CC=CC=C1 IRNJRGVFXLVQEK-UHFFFAOYSA-N 0.000 description 1
BSMGLVDZZMBWQB-UHFFFAOYSA-N 2-methyl-1-phenylpropan-1-one Chemical compound CC(C)C(=O)C1=CC=CC=C1 BSMGLVDZZMBWQB-UHFFFAOYSA-N 0.000 description 1
ZHSGKMPXEWBKBM-UHFFFAOYSA-N 3,4,5-trimethylthiophene-2-carboxylic acid Chemical compound CC=1SC(C(O)=O)=C(C)C=1C ZHSGKMPXEWBKBM-UHFFFAOYSA-N 0.000 description 1
HVMIFVYQHRBPHJ-UHFFFAOYSA-N 3-(2-methylpropyl)thiophene-2-carboxylic acid Chemical compound CC(C)CC=1C=CSC=1C(O)=O HVMIFVYQHRBPHJ-UHFFFAOYSA-N 0.000 description 1
MBXOOYPCIDHXGH-UHFFFAOYSA-N 3-butylpentane-2,4-dione Chemical compound CCCCC(C(C)=O)C(C)=O MBXOOYPCIDHXGH-UHFFFAOYSA-N 0.000 description 1
GUARKOVVHJSMRW-UHFFFAOYSA-N 3-ethylpentane-2,4-dione Chemical compound CCC(C(C)=O)C(C)=O GUARKOVVHJSMRW-UHFFFAOYSA-N 0.000 description 1
WQFHVSBZPSUVDD-UHFFFAOYSA-N 3-hydroxy-1-(4-methylphenyl)prop-2-en-1-one Chemical compound CC1=CC=C(C(=O)C=CO)C=C1 WQFHVSBZPSUVDD-UHFFFAOYSA-N 0.000 description 1
YIWTXSVNRCWBAC-UHFFFAOYSA-N 3-phenylpentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)C1=CC=CC=C1 YIWTXSVNRCWBAC-UHFFFAOYSA-N 0.000 description 1
PJCCSZUMZMCWSX-UHFFFAOYSA-N 4,4-Dimethoxy-2-butanone Chemical compound COC(OC)CC(C)=O PJCCSZUMZMCWSX-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
BXBJZYXQHHPVGO-UHFFFAOYSA-N 4-hydroxycyclohexan-1-one Chemical compound OC1CCC(=O)CC1 BXBJZYXQHHPVGO-UHFFFAOYSA-N 0.000 description 1
241000219307 Atriplex rosea Species 0.000 description 1
DBLPKRKIAKOASN-UHFFFAOYSA-N C(=O)(OC)CSC=CC(C)=O Chemical compound C(=O)(OC)CSC=CC(C)=O DBLPKRKIAKOASN-UHFFFAOYSA-N 0.000 description 1
YMERWJVXXVZOPU-UHFFFAOYSA-N C(C)(=O)O.C(C)(=O)O.C(C)(=O)CC(C)=O Chemical compound C(C)(=O)O.C(C)(=O)O.C(C)(=O)CC(C)=O YMERWJVXXVZOPU-UHFFFAOYSA-N 0.000 description 1
JKKPSQAOXKVTPK-UHFFFAOYSA-N CCOC(=O)C=1SC=C(C1C)C(C)=O Chemical compound CCOC(=O)C=1SC=C(C1C)C(C)=O JKKPSQAOXKVTPK-UHFFFAOYSA-N 0.000 description 1
SJVPTCHVUWWSAH-UHFFFAOYSA-N CCOC(CSC=CC(C)=O)=O Chemical compound CCOC(CSC=CC(C)=O)=O SJVPTCHVUWWSAH-UHFFFAOYSA-N 0.000 description 1
241000282376 Panthera tigris Species 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
UZTZDXILWKKQRB-UHFFFAOYSA-N ethyl 3-methylthiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC=CC=1C UZTZDXILWKKQRB-UHFFFAOYSA-N 0.000 description 1
230000029142 excretion Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
ILPNRWUGFSPGAA-UHFFFAOYSA-N heptane-2,4-dione Chemical compound CCCC(=O)CC(C)=O ILPNRWUGFSPGAA-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000006263 metalation reaction Methods 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
GJYXGIIWJFZCLN-UHFFFAOYSA-N octane-2,4-dione Chemical compound CCCCC(=O)CC(C)=O GJYXGIIWJFZCLN-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052573 porcelain Inorganic materials 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003577 thiophenes Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH7182959A 1958-04-12 1959-04-10 Verfahren zur Herstellung von Thiophencarbonsäuren und deren Estern CH378901A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF25480A DE1088507B (de)	1958-04-12	1958-04-12	Verfahren zur Herstellung von substituierten Thiophen-2-carbonsaeureestern bzw. den freien Carbonsaeuren

Publications (1)

Publication Number	Publication Date
CH378901A true CH378901A (de)	1964-06-30

Family

ID=7091653

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7182959A CH378901A (de)	1958-04-12	1959-04-10	Verfahren zur Herstellung von Thiophencarbonsäuren und deren Estern

Country Status (4)

Country	Link
BE (1)	BE577637R (fr)
CH (1)	CH378901A (fr)
DE (1)	DE1088507B (fr)
GB (1)	GB903951A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4496580A (en) *	1981-07-23	1985-01-29	Hoechst-Roussel Pharmaceuticals Inc.	Oxothienobenzoxepins

1958
- 1958-04-12 DE DEF25480A patent/DE1088507B/de active Pending
1959
- 1959-04-10 CH CH7182959A patent/CH378901A/de unknown
- 1959-04-13 GB GB1252859A patent/GB903951A/en not_active Expired
- 1959-04-13 BE BE577637A patent/BE577637R/fr active

Also Published As

Publication number	Publication date
DE1088507B (de)	1960-09-08
GB903951A (en)	1962-08-22
BE577637R (fr)	1959-10-13

Publication	Publication Date	Title
CH554821A (de)	1974-10-15	Verfahren zur herstellung von bis-stilbenverbindungen.
CH390277A (de)	1965-04-15	Verfahren zur Herstellung von 3,5-disubstituierten 4-Oxy-benzoesäurealkylestern
CH378901A (de)	1964-06-30	Verfahren zur Herstellung von Thiophencarbonsäuren und deren Estern
US3062834A (en)	1962-11-06	Process for preparing thiophencarboxylic acids and their esters
DE1055007B (de)	1959-04-16	Verfahren zur Herstellung von 3-Aminothiophen-2-carbonsaeureestern und den entsprechenden freien Carbonsaeuren
Hansch et al.	1955	SYNTHESIS OF 6-SUBSTITUTED THIANAPHTHENES1
DE1092929B (de)	1960-11-17	Verfahren zur Herstellung von substituierten Thiophen-2-carbonsaeureestern bzw. den freien Carbonsaeuren
EP0061669B1 (fr)	1984-07-25	Procédé de préparation de cyclohexane-1,3-diones, ainsi que cyclohexanes-1,3-diones bicycliques
DE2361144C3 (de)	1979-03-29	SuIfon-Alkohole und deren Ester und Verfahren zu ihrer Herstellung
DE958844C (de)	1957-02-28	Verfahren zur Herstellung von ª†-Acyl-buttersaeuren
US3691231A (en)	1972-09-12	New process for the preparation of 1-indancarboxylic acids
Lauer et al.	1939	The Rearrangement of Phenyl Allyl Ethers. V. The Isomeric Ethyl p-(α-and γ-Propylallyloxy)-benzoates
Thomas et al.	1934	The Acetoacetic Ester Condensation. VIII. The Condensation of ι-Piperidino Esters
AT227264B (de)	1963-05-10	Verfahren zur Herstellung von neuen Derivaten hydrierter Pyridone
AT211830B (de)	1960-11-10	Verfahren zur Herstellung von Thiophencarbonsäuren und deren Derivaten
AT259557B (de)	1968-01-25	Verfahren zur Herstellung von 3- Aminoisoxazolen
AT215993B (de)	1961-07-10	Verfahren zur Herstellung von neuen 4-Oxo-2-(halogenalkyl)-2,3-dihydro-[benzo-1,3-oxazinen]
Bachmann et al.	1941	The Synthesis of cis and trans 1-Methyl-cyclopentane-1, 2-dicarboxylic Acids and Related Compounds
DE862601C (de)	1953-01-12	Verfahren zur Herstellung neuer Diphenyl-(A2,3-2-methyl-propenyl)-essigsaeure-dialkylamino-alkylester und ihrer Salze
DE873242C (de)	1953-05-28	Verfahren zur Darstellung von Oestradiol bzw. seiner Derivate
AT235259B (de)	1964-08-25	Verfahren zur Herstellung von Polyencarbonylverbindungen
AT336004B (de)	1977-04-12	Verfahren zur herstellung neuer 3-(4-biphenylyl)-buttersauren, ihrer ester, amide und salze
DE2912052A1 (de)	1980-03-20	Verfahren zur herstellung von 2eckige klammer auf 4-(thienylcarbonyl)phenyl eckige klammer zu -propionsaeure
AT200152B (de)	1958-10-25	Verfahren zur Herstellung von neuen 4-Oxo-2-(halogenalkyl)-2, 3-dihydro-[benzo-1, 3-oxazinen]
DEC0010467MA (fr)