CH306569A - Process for the preparation of a mixture of cinnamic acid esters of polyethylene glycol monomethyl ethers. - Google Patents
Process for the preparation of a mixture of cinnamic acid esters of polyethylene glycol monomethyl ethers.Info
- Publication number
- CH306569A CH306569A CH306569DA CH306569A CH 306569 A CH306569 A CH 306569A CH 306569D A CH306569D A CH 306569DA CH 306569 A CH306569 A CH 306569A
- Authority
- CH
- Switzerland
- Prior art keywords
- mixture
- cinnamic acid
- glycol monomethyl
- polyethylene glycol
- preparation
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 title claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001851 cinnamic acid derivatives Chemical class 0.000 title description 3
- 150000002148 esters Chemical class 0.000 claims description 8
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 7
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 4
- 229930016911 cinnamic acid Natural products 0.000 claims description 4
- 235000013985 cinnamic acid Nutrition 0.000 claims description 4
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000723347 Cinnamomum Species 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- -1 cinnamic acid ester Chemical class 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
Description
v' Verfahren zur Herstellung eines Gemisches von Zimtsäureestern < Polyäthylenglykolmonomethyläthern.
Es wurde die überraschende Beobachtvmg gemacht, dass Ester aus Zimtsäure und Poly äthylenglykolmonomethyläthern der Formel
EMI1.1
worin n eine Zahl von 4 bis 50 bedeutet, wertvolle therapeutische Eigenschaften aufweisen.
Das vorliegende Patent bezieht sich auf ein Verfahren zur Herstellung eines Gemisches solcher Ester, welches Verfahren dadurch gekennzeichnet ist, dass man ein solches Gemisch von Polyäthylenglykolmonomethyläthern, aus welchem beim Verestern mit Zimtsä. ure ein wasserlösliches Estergemisch entsteht, mit den Zimtsäurerest abgebenden Verbindungen um setzt. Der Endstoff ist ein (il und ist in den meisten organischen Lösungsmitteln, mit Aus- nahme von aliphatischen Kohlenwasserstoffen, leicht loslich.
Als Ausgangsstoff fiir das neue Verfah ren geeignete Polyäthylenglykolmonomethyl- äther-Gemische sind technisch leicht zugäng- liel. Die Komponenten des Zimtsäureester (remisehes weisen bezüglich ihres Molekular gewiehtes eine ähnliche Verteilung wie die Komponenten des Ausgangsproduktes auf.
Als den Zimtsäurerest abgebende Verbin dungen sind beispielsweise geeignet Zimtsäure oder zum Beispiel ihre Ester mit nied rigmolekularen Alkoholen oder Halogenide, z. B. ihr Chlorid. Bei Verwendung des letzteren ist es zweckmässig, in der im folgenden Beispiel angegebenen Weise zu verfahren.
Das neue Estergemisch soll als Heilmittel verwendet werden.
Beispiel :
4,65 Gewichtsteile Zimtsäurechlorid und 8,1 Gewichtsteile Polyäthylenglykolmono- methyläther vom durchschnittlichen Molekulargewicht 350, bei 110 im Hochvakuum getrocknet, werden mit 25 Volumteilen absolutem Pyridin während einer Stunde auf 100 erhitzt. Nach dem Abkuhlen wird auf eine Mischung von 32 Volumteilen konzentrierter Salzsäure und 160 Gewichtsteilen feinem Eis ausgegossen. Darauf wird mit 200 Volumteilen Chloroform in einen Scheidetrichter gespült und die Chloroformlösung je zweimal mit 2n-Salzsäure, gesättigter Natriumhydro- gencarbonatlösung und halbgesättigter Koch- salzlosung gewaschen.
Beim Eindampfen der Chloroformlosung bleibt das rohe Gemisch der Zimtsäureester der Polyäthylenglykolmono- methyläther als hellbraunes, wasserlösliehes öl zurück. Es kann durch Behandlmg mit wenig Tierkohle in wässeriger Löslmg gereinigt werden.
Der neue Ester kann als Infiltrationsanästhetikum verwendet werden.
v 'Process for the preparation of a mixture of cinnamic acid esters <polyethylene glycol monomethyl ethers.
The surprising observation was made that esters of cinnamic acid and poly ethylene glycol monomethyl ethers of the formula
EMI1.1
where n is a number from 4 to 50, have valuable therapeutic properties.
The present patent relates to a process for the preparation of a mixture of such esters, which process is characterized in that such a mixture of polyethylene glycol monomethyl ethers, from which on esterification with cinnamon acid. ure a water-soluble ester mixture is formed, with the compounds releasing cinnamic acid residues. The end product is a (il and is easily soluble in most organic solvents, with the exception of aliphatic hydrocarbons.
Polyethylene glycol monomethyl ether mixtures suitable as starting material for the new process are readily available industrially. In terms of their molecular weight, the components of the cinnamic acid ester (remisehes) have a similar distribution to the components of the starting product.
Suitable compounds as the cinnamic acid residue are, for example, cinnamic acid or, for example, its esters with low molecular weight alcohols or halides, e.g. B. Their chloride. When using the latter, it is advisable to proceed in the manner indicated in the following example.
The new ester mixture is said to be used as a remedy.
Example:
4.65 parts by weight of cinnamic acid chloride and 8.1 parts by weight of polyethylene glycol monomethyl ether with an average molecular weight of 350, dried at 110 in a high vacuum, are heated to 100 with 25 parts by volume of absolute pyridine for one hour. After cooling, it is poured onto a mixture of 32 parts by volume of concentrated hydrochloric acid and 160 parts by weight of fine ice. Then it is rinsed with 200 parts by volume of chloroform into a separating funnel and the chloroform solution is washed twice each with 2N hydrochloric acid, saturated sodium hydrogen carbonate solution and semi-saturated sodium chloride solution.
When the chloroform solution is evaporated, the crude mixture of cinnamic acid esters and polyethylene glycol monomethyl ether remains as a light brown, water-soluble oil. It can be cleaned by treating it with a little animal charcoal in an aqueous solution.
The new ester can be used as an infiltration anesthetic.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH306569T | 1950-02-15 | ||
| CH298677T | 1952-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306569A true CH306569A (en) | 1955-04-15 |
Family
ID=25734016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306569D CH306569A (en) | 1950-02-15 | 1950-02-15 | Process for the preparation of a mixture of cinnamic acid esters of polyethylene glycol monomethyl ethers. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306569A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0044975A1 (en) * | 1980-07-26 | 1982-02-03 | BASF Aktiengesellschaft | Polyalkoxycarbinol esters of cinnamic acid, preparation and use in light-protective agents |
-
1950
- 1950-02-15 CH CH306569D patent/CH306569A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0044975A1 (en) * | 1980-07-26 | 1982-02-03 | BASF Aktiengesellschaft | Polyalkoxycarbinol esters of cinnamic acid, preparation and use in light-protective agents |
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