CH253189A - Process for making an ester. - Google Patents
Process for making an ester.Info
- Publication number
- CH253189A CH253189A CH253189DA CH253189A CH 253189 A CH253189 A CH 253189A CH 253189D A CH253189D A CH 253189DA CH 253189 A CH253189 A CH 253189A
- Authority
- CH
- Switzerland
- Prior art keywords
- ester
- toluic acid
- act
- reaction
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000002148 esters Chemical class 0.000 title claims description 8
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- -1 o-toluic acid halide Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims 1
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung eines Esters. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Esters. Das Verfahren ist dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI0001.0005
auf eine Verbindung der Formel
EMI0001.0006
worin X und Y reaktionsfähige, mit Aus nahme eines in einem von ihnen enthaltenen Sauerstoffatoms sich bei der Reaktion ab spaltende Reste bedeuten, einwirken lässt.
Die entstandene neue Verbindung, der o-To- luylsäure-a-äthyl-benzylester, siedet unter 0,3 min Druck bei 129-131 . Sie soll als Arzneimittel Verwendung finden.
Beispiel: Mrerden <B>15</B> Teile o-Toluylsäurechlorid in Cxegenwart von 8 Teilen Pyridin mit a-Äthyl- benzylalkohol in Reaktion gebracht, so er hält man den o-Toluylsäureester des a-Äthyl- benzylalkohols als farbloses Öl vom Siede punkt 129-131 unter 0,3 mm Druck.
Statt von o-Toluylsäurechlorid kann man aueh. vom Anhydrid oder von einem Ester der o-Toluylsäure mit einem niederen Al kohol ausgehen und diese mit a-Äthyl- benzylalkoliol umsetzen; oder man verestert die o-Toluylsäure mit a-Äthyl-benzylalkohol in Gegenwart eines Kondensationsmittels, wie Halogenwasserstoffsäure oder Schwefelsäure.
Zum gleichen Endprodukt gelangt man ferner durch Einwirkenlassen von einem o-toluylsauren Salz auf einen reaktions fähigen Ester des a-Äthyl-benzylalkohols, wie z. B. einen Halogenwasserstoffsäureester oder einen aromatischen Sulfonsäureester.
Process for making an ester. The present patent is a process for the preparation of an ester. The process is characterized in that a compound of the formula
EMI0001.0005
to a compound of the formula
EMI0001.0006
wherein X and Y are reactive, with the exception of an oxygen atom contained in one of them can mean cleaving radicals in the reaction.
The resulting new compound, the o-toluic acid a-ethyl-benzyl ester, boils under 0.3 min pressure at 129-131. It should be used as a medicine.
Example: Bringing 15 parts of o-toluic acid chloride in the presence of 8 parts of pyridine with a-ethylbenzyl alcohol, the o-toluic acid ester of a-ethylbenzyl alcohol is kept boiling as a colorless oil point 129-131 under 0.3 mm pressure.
Instead of o-toluic acid chloride one can also use start from the anhydride or from an ester of o-toluic acid with a lower alcohol and react this with a-ethylbenzyl alcohol; or the o-toluic acid is esterified with a-ethylbenzyl 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-toluic acid salt to act on a reactive ester of a-ethyl 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 | ||
| CH253189T | 1944-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253189A true CH253189A (en) | 1948-02-15 |
Family
ID=25729721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253189D CH253189A (en) | 1943-11-26 | 1944-12-21 | Process for making an ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253189A (en) |
-
1944
- 1944-12-21 CH CH253189D patent/CH253189A/en unknown
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