CH447200A - Procédé de préparation des acides carboxyliques a-substitués - Google Patents
Procédé de préparation des acides carboxyliques a-substituésInfo
- Publication number
- CH447200A CH447200A CH245966A CH245966A CH447200A CH 447200 A CH447200 A CH 447200A CH 245966 A CH245966 A CH 245966A CH 245966 A CH245966 A CH 245966A CH 447200 A CH447200 A CH 447200A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- preparation
- acid
- alcohol
- carboxylic acids
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000001735 carboxylic acids Chemical class 0.000 title claims description 5
- 239000002253 acid Substances 0.000 claims description 22
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- -1 disubstituted alkyl malonate Chemical compound 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 102220347004 c.89G>A Human genes 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 description 2
- 102000004895 Lipoproteins Human genes 0.000 description 2
- 108090001030 Lipoproteins Proteins 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- LUKDALDUKVBQLO-UHFFFAOYSA-N 2-(2-phenylphenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=CC=C1C1=CC=CC=C1 LUKDALDUKVBQLO-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- OFGXPNKHTXDEBE-UHFFFAOYSA-N 3-ethoxy-3-oxo-2-(oxolan-2-ylmethyl)propanoic acid Chemical compound CCOC(=O)C(CC1CCCO1)C(O)=O OFGXPNKHTXDEBE-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical class CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- 244000126014 Valeriana officinalis Species 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000036765 blood level Effects 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
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001989 choleretic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 230000000260 hypercholesteremic effect Effects 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000020075 ouzo Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR853642A FR1289597A (fr) | 1961-02-23 | 1961-02-23 | Nouveaux acides carboxyliques alpha-substitués par au moins un radical cyclique et leurs procédés de préparation |
| FR860401A FR80103E (fr) | 1961-02-23 | 1961-04-28 | Nouveaux acides carboxyliques alpha-substitués par au moins un radical cyclique et leurs procédés de préparation |
| FR862174A FR1318M (fr) | 1961-05-16 | 1961-05-16 | Nouveaux acides carboxyliques alpha-substitués a propriétés hypocholésterolémiantes. |
| FR885619A FR81162E (fr) | 1962-01-23 | 1962-01-23 | Nouveaux acides carboxyliques alpha-substitués par au moins un radical cyclique et leurs procédés de préparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH447200A true CH447200A (fr) | 1967-11-30 |
Family
ID=27445280
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH245966A CH447200A (fr) | 1961-02-23 | 1962-02-01 | Procédé de préparation des acides carboxyliques a-substitués |
| CH128462A CH464172A (fr) | 1961-02-23 | 1962-02-01 | Procédé de préparation d'acides carboxyliques -substitués |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH128462A CH464172A (fr) | 1961-02-23 | 1962-02-01 | Procédé de préparation d'acides carboxyliques -substitués |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3257420A (enrdf_load_stackoverflow) |
| BE (1) | BE613547A (enrdf_load_stackoverflow) |
| CH (2) | CH447200A (enrdf_load_stackoverflow) |
| DE (3) | DE1693019B2 (enrdf_load_stackoverflow) |
| GB (1) | GB999589A (enrdf_load_stackoverflow) |
| NL (1) | NL274986A (enrdf_load_stackoverflow) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3445574A (en) * | 1962-09-20 | 1969-05-20 | Lipha | Compositions and method for arresting spasms with the diethylaminoethyl ester of beta-(1-naphthyl)-beta'-tetrahydrofurylisobutyric acid |
| NL295854A (enrdf_load_stackoverflow) * | 1962-12-04 | |||
| GB1217689A (en) * | 1967-08-14 | 1970-12-31 | Guppo Lepetit S P A | Ethyl esters of fluro-acetic acids |
| DE2003363A1 (de) | 1969-01-30 | 1970-08-06 | Ciba Geigy | Verfahren zum Faerben und Bedrucken von Textilien mit Kuepen- und Reaktivfarbstoffen |
| US3686307A (en) * | 1969-02-07 | 1972-08-22 | Standard Oil Co | Conversion of nitriles to amides in the presence of alkaline catalysts |
| US3956323A (en) * | 1972-01-03 | 1976-05-11 | Hoffmann-La Roche Inc. | Furan, benzofuran and tetrahydrofuran carboxylic acid esters |
| GB1540917A (en) * | 1976-08-06 | 1979-02-21 | Wassermann Spa A | Furan derivatives for use as pharmaceutical products particularly for the treatment of rheumatic illnesses and a method for their preparation |
| DE2733181B2 (de) * | 1977-07-22 | 1979-08-30 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von N-substituierten a -Ketocarbonsäureamiden |
| FR2580502B1 (fr) * | 1985-04-23 | 1988-07-08 | Lipha | Emploi du " naftidrofuryl " dans la preparation d'un medicament |
| US5329054A (en) * | 1993-07-19 | 1994-07-12 | Albemarle Corporation | Decarboxylation process |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2841594A (en) * | 1958-07-01 | Production of beta-furoic acids | ||
| US2937117A (en) * | 1953-06-19 | 1960-05-17 | Chimie Atomistique | Process for lowering high blood cholesterol levels |
| FR1109144A (fr) * | 1954-07-13 | 1956-01-23 | Air Liquide | Procédé de préparation d'esters |
| US2834789A (en) * | 1955-02-15 | 1958-05-13 | Sadolin & Holmblad As | Process of preparing lower lakyl 2, 3, 6-trihydroxybenzoate, and intermediates therefor |
| US3057777A (en) * | 1957-10-28 | 1962-10-09 | Lilly Co Eli | Method of reducing cholesterol level of the blood |
| US3013023A (en) * | 1959-02-27 | 1961-12-12 | Ueno Ryuzo | Process for the production of 5-nitrofuryl acrylic acid |
| US3060198A (en) * | 1959-10-06 | 1962-10-23 | Du Pont | Tetracyanofuran |
-
0
- NL NL274986D patent/NL274986A/xx unknown
-
1962
- 1962-02-01 CH CH245966A patent/CH447200A/fr unknown
- 1962-02-01 CH CH128462A patent/CH464172A/fr unknown
- 1962-02-06 BE BE613547A patent/BE613547A/fr unknown
- 1962-02-16 GB GB6141/62A patent/GB999589A/en not_active Expired
- 1962-02-17 DE DE1693019*CA patent/DE1693019B2/de active Granted
- 1962-02-21 US US174684A patent/US3257420A/en not_active Expired - Lifetime
- 1962-12-17 DE DE1962L0041255 patent/DE1493912A1/de active Pending
-
1964
- 1964-11-13 DE DE1964L0049288 patent/DE1493933A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US3257420A (en) | 1966-06-21 |
| DE1693019B2 (de) | 1975-11-13 |
| BE613547A (fr) | 1962-08-06 |
| DE1493933A1 (de) | 1969-06-04 |
| GB999589A (enrdf_load_stackoverflow) | 1965-07-28 |
| CH464172A (fr) | 1968-10-31 |
| NL274986A (enrdf_load_stackoverflow) | |
| DE1693019A1 (de) | 1972-03-30 |
| DE1493912A1 (de) | 1969-07-10 |
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