CH443350A - Verfahren zur Herstellung von neuen Salicylsäure-Derivaten - Google Patents
Verfahren zur Herstellung von neuen Salicylsäure-DerivatenInfo
- Publication number
- CH443350A CH443350A CH348263A CH348263A CH443350A CH 443350 A CH443350 A CH 443350A CH 348263 A CH348263 A CH 348263A CH 348263 A CH348263 A CH 348263A CH 443350 A CH443350 A CH 443350A
- Authority
- CH
- Switzerland
- Prior art keywords
- salicylic acid
- methyl
- acid derivatives
- production
- xylene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 title claims description 5
- 150000003872 salicylic acid derivatives Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000001569 carbon dioxide Substances 0.000 claims description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 23
- 229960004889 salicylic acid Drugs 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- -1 salicylic acid derivatives Salicylic acids Chemical class 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 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 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- DZZPJWJPJJNWHM-UHFFFAOYSA-N 2-hydroxy-3-(1-phenylethyl)benzoic acid Chemical compound C=1C=CC(C(O)=O)=C(O)C=1C(C)C1=CC=CC=C1 DZZPJWJPJJNWHM-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GVZMSQZBRPXEGK-UHFFFAOYSA-N 2-hydroxy-3-(1-phenylprop-2-enyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C(C=C)C2=CC=CC=C2)=C1O GVZMSQZBRPXEGK-UHFFFAOYSA-N 0.000 description 2
- VAYMEJTVMQWPBZ-UHFFFAOYSA-N 3-[1-(4-chlorophenyl)ethyl]-2-hydroxybenzoic acid Chemical compound C=1C=CC(C(O)=O)=C(O)C=1C(C)C1=CC=C(Cl)C=C1 VAYMEJTVMQWPBZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HKNDKNUNEABACI-UHFFFAOYSA-N CC(C(C=CC=C1)=C1OC)C(C=CC=C1C(O)=O)=C1O Chemical compound CC(C(C=CC=C1)=C1OC)C(C=CC=C1C(O)=O)=C1O HKNDKNUNEABACI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000021523 carboxylation Effects 0.000 description 2
- 238000006473 carboxylation reaction Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QYPBOXRMLFPDEQ-UHFFFAOYSA-N 2-(1-phenylethenyl)phenol Chemical compound OC1=CC=CC=C1C(=C)C1=CC=CC=C1 QYPBOXRMLFPDEQ-UHFFFAOYSA-N 0.000 description 1
- CPIXGYKQJSHWGS-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)ethyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C)C1=CC=C(Cl)C=C1 CPIXGYKQJSHWGS-UHFFFAOYSA-N 0.000 description 1
- VPTXPMBNBZLRET-UHFFFAOYSA-N 2-hydroxy-3-(3-phenylpropyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(CCCC=2C=CC=CC=2)=C1O VPTXPMBNBZLRET-UHFFFAOYSA-N 0.000 description 1
- BXQSMDCMQRISEC-UHFFFAOYSA-N 2-hydroxy-5-methyl-3-(1-phenylethyl)benzoic acid Chemical compound C=1C(C)=CC(C(O)=O)=C(O)C=1C(C)C1=CC=CC=C1 BXQSMDCMQRISEC-UHFFFAOYSA-N 0.000 description 1
- CKDMFIHYMJZAIL-UHFFFAOYSA-N 2-hydroxy-6-methyl-3-(1-phenylethyl)benzoic acid Chemical compound C=1C=C(C)C(C(O)=O)=C(O)C=1C(C)C1=CC=CC=C1 CKDMFIHYMJZAIL-UHFFFAOYSA-N 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- LHSIUQJHRFFBPW-UHFFFAOYSA-N CC(C1=C(C)C=CC=C1)C(C=CC=C1C(O)=O)=C1O Chemical compound CC(C1=C(C)C=CC=C1)C(C=CC=C1C(O)=O)=C1O LHSIUQJHRFFBPW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
- C07C47/57—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/19—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups having unsaturation outside the aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB66450A DE1198831B (de) | 1962-03-21 | 1962-03-21 | Verfahren zur Herstellung von 3-Aralkylsalicylsaeuren |
| DEB69969A DE1216293B (de) | 1962-12-13 | 1962-12-13 | Verfahren zur Herstellung von 3-Phenylalkenyl-salicylsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH443350A true CH443350A (de) | 1967-09-15 |
Family
ID=25966191
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH348263A CH443350A (de) | 1962-03-21 | 1963-03-19 | Verfahren zur Herstellung von neuen Salicylsäure-Derivaten |
| CH1253966A CH479526A (de) | 1962-03-21 | 1963-03-19 | Verfahren zur Herstellung von substituierten Salicylsäuren |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1253966A CH479526A (de) | 1962-03-21 | 1963-03-19 | Verfahren zur Herstellung von substituierten Salicylsäuren |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT243785B (en:Method) |
| CH (2) | CH443350A (en:Method) |
| DK (2) | DK109782C (en:Method) |
| FI (2) | FI40720B (en:Method) |
| GB (1) | GB966479A (en:Method) |
| LU (1) | LU43384A1 (en:Method) |
| SE (1) | SE312142B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004058679A3 (en) * | 2002-12-20 | 2004-08-26 | Mitokor Inc | Ligands of adenine nucleotide translocase (ant) and compositions and methods related thereto |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4687869A (en) * | 1984-10-22 | 1987-08-18 | Ciba-Geigy Corporation | Metal salicylates, process for their preparation and use thereof as color developers in pressure-sensitive or heat-sensitive recording materials |
-
1963
- 1963-03-01 GB GB830463A patent/GB966479A/en not_active Expired
- 1963-03-14 FI FI49763A patent/FI40720B/fi active
- 1963-03-19 CH CH348263A patent/CH443350A/de unknown
- 1963-03-19 CH CH1253966A patent/CH479526A/de not_active IP Right Cessation
- 1963-03-19 LU LU43384D patent/LU43384A1/xx unknown
- 1963-03-20 AT AT220563A patent/AT243785B/de active
- 1963-03-20 DK DK560965A patent/DK109782C/da active
- 1963-03-20 DK DK127363A patent/DK109147C/da active
-
1965
- 1965-06-15 SE SE787865A patent/SE312142B/xx unknown
-
1968
- 1968-08-15 FI FI231568A patent/FI42093C/fi active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004058679A3 (en) * | 2002-12-20 | 2004-08-26 | Mitokor Inc | Ligands of adenine nucleotide translocase (ant) and compositions and methods related thereto |
Also Published As
| Publication number | Publication date |
|---|---|
| FI40720B (en:Method) | 1969-01-31 |
| DK109147C (da) | 1968-03-25 |
| FI42093C (fi) | 1970-05-11 |
| CH479526A (de) | 1969-10-15 |
| FI42093B (en:Method) | 1970-02-02 |
| DK109782C (da) | 1968-07-01 |
| GB966479A (en) | 1964-08-12 |
| LU43384A1 (en:Method) | 1963-05-20 |
| AT243785B (de) | 1965-11-25 |
| SE312142B (en:Method) | 1969-07-07 |
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