CH253190A - Process for making an ester. - Google Patents
Process for making an ester.Info
- Publication number
- CH253190A CH253190A CH253190DA CH253190A CH 253190 A CH253190 A CH 253190A CH 253190D A CH253190D A CH 253190DA CH 253190 A CH253190 A CH 253190A
- Authority
- CH
- Switzerland
- Prior art keywords
- ester
- compound
- reaction
- alcohol
- formula
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- KJRRTHHNKJBVBO-AATRIKPKSA-N (e)-3-(2-chlorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1Cl KJRRTHHNKJBVBO-AATRIKPKSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- -1 o-chlorocinnamic acid halide Chemical class 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
- 239000011230 binding agent Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- ZAUFNZFFWDQKPL-UHFFFAOYSA-N 3-(2-chlorophenyl)prop-2-enoyl chloride Chemical compound ClC(=O)C=CC1=CC=CC=C1Cl ZAUFNZFFWDQKPL-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 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
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Esters. Cregenstan d vorliegenden Patentes ist ein Verl'@tliren zur Herstellung eines Esters. Das Verfahren ist dadurch gekennzeichnet, dass itian eine Verbindung der Formel
EMI0001.0007
-ini' eine Verbindung der Formel
EMI0001.0009
Torin X und Y reaktionsfähige, mit Aus- n;ilime eines in einem von ihnen enthaltenen Satifrstoffatoms sich bei der Reaktion ab spaltende Reste bedeuten, einwirken lässt.
I)ie entstandene neue Verbindung, der o-Chlor- zimtsäure-u-n-butyl-benzylester, siedet bei 187--..190" unter 0,2 mm Druck. Sie soll als Arzneimittel Verwendung finden.
<I>Beispiel:</I> ?0,1 Teile o-Chlor-zimtsäurechlorid wer den mit<B>1.7</B> Teilen a-n-Butyl-benzylalkohol in Gz-genwart von 8 Teilen Pyridin umgesetzt.
Nach mehrstiindigem Erhitzen auf kochen dem Wasserbad wird die Mischung mit Xtlier und Wasser versetzt, die Ätherlösung finit Wasser und verdünntem Alkali ge- waschen, getrocknet und der Äther abdestil- liert. Man erhält den o-Chlor-zimtsä,ureester des a-n-Butyl-benzylalkohols vom Siede punkt 18i-190" unter 0,2 mm Druck. Man kann auch ohne Zusatz von Pyridin arbeiten. In diesem Falle wird erhitzt, bis die Chlorwasserstoffentwicklung beendet ist.
Statt vom o-Chlor-zimtsäurechlorid kann man auch vom Anhydrid oder von einem Ester der Zimtsäure mit einem niederen Al kohol ausgehen und diese mit a-n-Butyl- benzylalkohol umsetzen; oder man verestert die Zimtsäure mit a-n-Butyl-benzylalkohol in Gegenwart eines Kondensationsmittels, wie Halogenwasserstoffsäure oder Schwefelsäure.
Zum gleichen Endprodukt gelangt man ferner durch Einwirkenlassen von einem o-chlor-zimtsauren Salz auf einen reaktions fähigen Ester des a-n-Butyl-benzylalkohols, wie z. B. einen Halogenwasserstoffsäureester oder einen aromatischen Sulfonsäureester.
Process for making an ester. Cregenstan d present patent is a Verl '@ tliren for the production of an ester. The method is characterized in that itian a compound of the formula
EMI0001.0007
-ini 'a compound of the formula
EMI0001.0009
Torin X and Y reactive, with the exception of a satellite atom contained in one of them can mean splitting off residues during the reaction.
The resulting new compound, the o-chlorocinnamic acid-u-n-butyl-benzyl ester, boils at 187-190 "under 0.2 mm pressure. It is said to be used as a medicinal product.
<I> Example: </I>? 0.1 part of o-chloro-cinnamic acid chloride are reacted with <B> 1.7 </B> parts of a-n-butylbenzyl alcohol in the presence of 8 parts of pyridine.
After several hours of heating to the boil in a water bath, the mixture is mixed with Xtlier and water, the ether solution is washed with water and dilute alkali, dried, and the ether is distilled off. The o-chloro-cinnamic acid ester of an-butylbenzyl alcohol with a boiling point of 18-190 "is obtained under 0.2 mm pressure. It is also possible to work without the addition of pyridine. In this case, the mixture is heated until the evolution of hydrogen chloride has ceased .
Instead of the o-chloro-cinnamic acid chloride, one can also start from the anhydride or from an ester of cinnamic acid with a lower alcohol and react this with a-n-butylbenzyl alcohol; or the cinnamic acid is esterified with a-n-butylbenzyl alcohol in the presence of a condensing agent such as hydrohalic acid or sulfuric acid.
The same end product is also obtained by allowing an o-chloro-cinnamic acid salt to act on a reactive ester of a-n-butyl-benzyl alcohol, such as. B. a hydrohalic acid ester or an aromatic sulfonic acid ester.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR922081X | 1943-11-26 | ||
| CH253190T | 1944-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253190A true CH253190A (en) | 1948-02-15 |
Family
ID=25729722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253190D CH253190A (en) | 1943-11-26 | 1944-12-21 | Process for making an ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253190A (en) |
-
1944
- 1944-12-21 CH CH253190D patent/CH253190A/en unknown
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