CH187894A - Process for the preparation of a dialdehyde. - Google Patents
Process for the preparation of a dialdehyde.Info
- Publication number
- CH187894A CH187894A CH187894DA CH187894A CH 187894 A CH187894 A CH 187894A CH 187894D A CH187894D A CH 187894DA CH 187894 A CH187894 A CH 187894A
- Authority
- CH
- Switzerland
- Prior art keywords
- dialdehyde
- preparation
- oxidizing agent
- formula
- process according
- Prior art date
Links
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 241000394605 Viola striata Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical group N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
verfahren zur Darstellung eines Dialdehydes. Gegenstand der vorliegenden Erfindung bildet ein Verfahren zur Darstellung eines Dialdehydes, welches dadurch gekennzeich net ist, @dass man auf Dihydroshikimisäure- methylester der Formel
EMI0001.0007
ein Oxydationsmittel einwirken lässt. Geeignete Oxydationsmittel sind zum Beispiel die Perhalogensäuren, insbesondere die Perjodsäure.
Der so erhaltene Dialdehyd der Formel
EMI0001.0014
ist in Wasser leicht löslich und bildet ein Bis - p - Nitrophenyl - hydrazonderivat vom F. 155 bis 160<B>0</B>.
Er kann als Ausgangsmaterial zur Her stellung pharmazeutischer Produkte dienen. <I>Beispiel:</I> 1 Teil Dihydroshikimisäure-methylester wird in Eiswasser gelöst und mit 10 Teilen einer wässerigen Perjodsäurelösung versetzt, deren Oxydationswert 2 Atomen Sauerstoff entspricht. Nach kurzer Zeit ist die Haupt reaktion vorbei. Nun gibt man fein zerrie benes und in Wasser aufgeschlämmtes Silber acetat hinzu und schüttelt, bis alle Jodsäure an Silber gebunden ist und die Flüssigkeit Kongopapier nur noch schwach violett färbt.
Nach dem Absaugen der .Silbersalze er hält man eine Lösung, aus der sich der Me- thylester des Tricarballylsäure-1.5-dial.de- hyds als Bis-p-Nitrophenylhydrazon fällen lässt.
process for the preparation of a dialdehyde. The subject of the present invention is a process for the preparation of a dialdehyde, which is characterized by using methyl dihydroshikimate of the formula
EMI0001.0007
allows an oxidizing agent to act. Suitable oxidizing agents are, for example, the perhalic acids, especially periodic acid.
The dialdehyde of the formula obtained in this way
EMI0001.0014
is easily soluble in water and forms a bis-p-nitrophenyl-hydrazone derivative with a melting point of 155 to 160 <B> 0 </B>.
It can be used as a starting material for the manufacture of pharmaceutical products. <I> Example: </I> 1 part of methyl dihydroshikimate is dissolved in ice water and mixed with 10 parts of an aqueous periodic acid solution, the oxidation value of which corresponds to 2 atoms of oxygen. After a short time, the main reaction is over. Now add finely ground silver acetate slurried in water and shake until all the iodic acid is bound to silver and the liquid only turns Congo paper a pale violet color.
After the silver salts have been filtered off with suction, a solution is obtained from which the methyl ester of tricarballylic acid-1,5-dialde-hydra can be precipitated as bis-p-nitrophenylhydrazone.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH183194T | 1934-09-22 | ||
| CH187894T | 1934-09-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH187894A true CH187894A (en) | 1936-11-30 |
Family
ID=25720831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH187894D CH187894A (en) | 1934-09-22 | 1934-09-22 | Process for the preparation of a dialdehyde. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH187894A (en) |
-
1934
- 1934-09-22 CH CH187894D patent/CH187894A/en unknown
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