ES455064A1 - Nuevo procedimiento para la obtencion del acido (d)-2(6-me- toxi-2-naftil)-propionico. - Google Patents
Nuevo procedimiento para la obtencion del acido (d)-2(6-me- toxi-2-naftil)-propionico.Info
- Publication number
- ES455064A1 ES455064A1 ES77455064A ES455064A ES455064A1 ES 455064 A1 ES455064 A1 ES 455064A1 ES 77455064 A ES77455064 A ES 77455064A ES 455064 A ES455064 A ES 455064A ES 455064 A1 ES455064 A1 ES 455064A1
- Authority
- ES
- Spain
- Prior art keywords
- propanal
- isomer
- give
- acid
- propionic acid
- 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 abstract 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 150000007857 hydrazones Chemical class 0.000 abstract 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 239000005708 Sodium hypochlorite Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Substances OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- 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
- C07C51/29—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with halogen-containing compounds which may be formed in situ
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
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)
Abstract
Nuevo procedimiento para la obtención del ácido (d)-2(6-metoxi-2-naftil)-propiónico, caracterizado por la realización de la siguiente sucesión de operaciones: a) Condensación del 2(6-metoxi-2-naftil)-propal racémico con la 5(alfa-feniletil)-semioxamacida dextrógira, en medio bencénico anhidro y en presencia de yodo como catalizador, para formar la mezcla diastereoisómera de semioxamazonas: **(Fórmula)** b) Resolución de la mezcla diastereoisómera de semioxamazonas obtenida, mediante recristalizaciones en dioxano, para separar el isómero d,d III puro, reservando las aguas madres conteniendo el isómero 1,d III para su recuperación si se desea; c) Hidrólisis del isómero d,d III separado bajo la acción del ácido sulfúrico al 20 % para liberar el isómero dextrogiro del 2(6-metoxi-2-naftil)-propanal; d) Oxidación del aldehido dextrógiro obtenido, utilizando como oxidante una solución de clorito sódico en presencia de ácido sulfámico, para obtener el producto final deseado (-acido 2(6-metoxi-2-naftil)-propiónico dextrógiro)).
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES77455064A ES455064A1 (es) | 1977-01-17 | 1977-01-17 | Nuevo procedimiento para la obtencion del acido (d)-2(6-me- toxi-2-naftil)-propionico. |
| DK179377A DK179377A (da) | 1977-01-17 | 1977-04-22 | Fremgangsmaade til fremstilling af (d)-2(6-methoxy-2-naphthyl) -propionsyre |
| FI771328A FI771328A7 (fi) | 1977-01-17 | 1977-04-26 | Nytt foerfarande foer framstaellning av (d)-2(6-metoxi-2-naftyl)propionsyra |
| FR7735102A FR2377370A1 (fr) | 1977-01-17 | 1977-11-15 | Procede pour l'obtention de l'acide (d)-2(6-methoxy-2-naphtyl)-propionique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES77455064A ES455064A1 (es) | 1977-01-17 | 1977-01-17 | Nuevo procedimiento para la obtencion del acido (d)-2(6-me- toxi-2-naftil)-propionico. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES455064A1 true ES455064A1 (es) | 1978-02-01 |
Family
ID=8472965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES77455064A Expired ES455064A1 (es) | 1977-01-17 | 1977-01-17 | Nuevo procedimiento para la obtencion del acido (d)-2(6-me- toxi-2-naftil)-propionico. |
Country Status (4)
| Country | Link |
|---|---|
| DK (1) | DK179377A (es) |
| ES (1) | ES455064A1 (es) |
| FI (1) | FI771328A7 (es) |
| FR (1) | FR2377370A1 (es) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0081993A3 (en) * | 1981-12-11 | 1984-01-11 | Syntex Pharmaceuticals International Limited | Optically active alpha-substituted aryl ketones, their preparation and their use in preparing alpha-arylalkanoic acids |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5210258A (en) * | 1981-12-11 | 1993-05-11 | Syntex Pharmaceuticals International Ltd. | Optically active alpha-naththylalkyl ketones |
| US4749804A (en) * | 1981-12-11 | 1988-06-07 | Syntex (U.S.A.) Inc. | Preparation of stereoisomers of ketals |
-
1977
- 1977-01-17 ES ES77455064A patent/ES455064A1/es not_active Expired
- 1977-04-22 DK DK179377A patent/DK179377A/da unknown
- 1977-04-26 FI FI771328A patent/FI771328A7/fi not_active Application Discontinuation
- 1977-11-15 FR FR7735102A patent/FR2377370A1/fr not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0081993A3 (en) * | 1981-12-11 | 1984-01-11 | Syntex Pharmaceuticals International Limited | Optically active alpha-substituted aryl ketones, their preparation and their use in preparing alpha-arylalkanoic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| FI771328A7 (fi) | 1978-07-15 |
| DK179377A (da) | 1978-07-15 |
| FR2377370A1 (fr) | 1978-08-11 |
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