CH233765A - Process for the preparation of α- (4-oxy-3,5-diiodophenyl) -a-phenyl-propionic acid. - Google Patents
Process for the preparation of α- (4-oxy-3,5-diiodophenyl) -a-phenyl-propionic acid.Info
- Publication number
- CH233765A CH233765A CH233765DA CH233765A CH 233765 A CH233765 A CH 233765A CH 233765D A CH233765D A CH 233765DA CH 233765 A CH233765 A CH 233765A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- oxy
- diiodophenyl
- propionic acid
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001875 compounds Chemical group 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ITATYELQCJRCCK-UHFFFAOYSA-N Mandelic Acid, Methyl Ester Chemical compound COC(=O)C(O)C1=CC=CC=C1 ITATYELQCJRCCK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- ZVAKTWSQIIRIIH-UHFFFAOYSA-N [K].[I] Chemical compound [K].[I] ZVAKTWSQIIRIIH-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- -1 diiodophenyl Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- 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
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung der a-(4-Ozy-3,5-dijod-phenyl)-a-phenyl-propionsäure. Gegenstand! des vorliegenden Patentes ist ein Verfahren zur Herstellung der a-(4-Oxy- 3,5-,dijod-phenyl)-a-phenyl-p.ropions@äure, das dadurch gekennzeichnet ist, dass man a-(4- Oxy - phenyl) - a - phenyl - propionsäure mit einem jodierenden Mittel behandelt.
Die neue Verbindung soll insbesondere als Gallenkontrastmittel Verwendung finden. abgesaugt und mit Wasser ausgewaschen.
Die nach dem Trocknen aus Benzol zweimal umkristallisierte a-(4-Oxy-3,5-@dijod-phenyl)- a-plhenyl-propionLäure, :ist ein farblos Kristallpulver. Sie schmilzt bei 183-184 . Sie ist leicht löslich in Äthier, Alkohol und Aceton, schwerer in Benzol, unlöslich in Wassier und Ligroin. <I>Beispiel:
</I> 24,2 g a-(4-Oxy-phenyl)-a-phenyl-pro- pionsäure vom Smp. 150 (hergestellt durch Kondensation von Methylmandelsäure und Phenol mit 73 % iger Schwefelsäure) werden in 800 cm' n/2 Natronlauge gelöst und unter c Rühren langsam bei gewöhnlicher Tempera tur mit einer Lösung von 50,8 g Jod und 50,8 Jodkalium .in 250 em3 Wasser versetzt.
Aus der annähernd neutralen, schwach ge färbten Lösung wird das Jodierungsprodukt : durch Zusatz von schwefliger Säure und Salzsäure ausgefällt. Es wird noch eine Zeit lang gerührt, das fast farblose Produkt ,dann
Process for the preparation of α- (4-Ozy-3,5-diiodophenyl) -a-phenyl-propionic acid. Object! of the present patent is a process for the preparation of a- (4-oxy-3,5-, diiodophenyl) -a-phenyl-p.ropionic acid, which is characterized in that a- (4-oxy - phenyl) - a - phenyl - propionic acid treated with an iodine agent.
The new compound is intended to be used in particular as a biliary contrast medium. Aspirated and washed out with water.
After drying, a- (4-oxy-3,5- @ diiodophenyl) - a-phenyl-propionic acid,: recrystallized twice from benzene, is a colorless crystal powder. It melts at 183-184. It is easily soluble in ethers, alcohol and acetone, more difficult in benzene, insoluble in water and ligroin. <I> example:
</I> 24.2 g of a- (4-oxy-phenyl) -a-phenyl-propionic acid with a melting point of 150 (produced by condensation of methylmandelic acid and phenol with 73% sulfuric acid) are in 800 cm 'n / 2 Sodium hydroxide solution and slowly mixed with a solution of 50.8 g of iodine and 50.8 g of iodine potassium in 250 cubic meters of water while stirring at normal temperature.
From the nearly neutral, slightly colored solution, the iodination product is: precipitated by adding sulfurous acid and hydrochloric acid. It is stirred for a while, then the almost colorless product
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE233765X | 1939-12-18 | ||
| CH220592T | 1940-05-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH233765A true CH233765A (en) | 1944-08-15 |
Family
ID=25726462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH233765D CH233765A (en) | 1939-12-18 | 1940-05-18 | Process for the preparation of α- (4-oxy-3,5-diiodophenyl) -a-phenyl-propionic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH233765A (en) |
-
1940
- 1940-05-18 CH CH233765D patent/CH233765A/en unknown
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