DE266120C - - Google Patents
Info
- Publication number
- DE266120C DE266120C DENDAT266120D DE266120DA DE266120C DE 266120 C DE266120 C DE 266120C DE NDAT266120 D DENDAT266120 D DE NDAT266120D DE 266120D A DE266120D A DE 266120DA DE 266120 C DE266120 C DE 266120C
- Authority
- DE
- Germany
- Prior art keywords
- lactic acid
- alkyl
- lactate
- esters
- acid esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- -1 alkyl lactic acid esters Chemical class 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 150000003903 lactic acid esters Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N Silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims 2
- 229910001923 silver oxide Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-(1R,3R,4S)-menthol Chemical group CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N Ethyl lactate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 229940100198 ALKYLATING AGENTS Drugs 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N Ethyl iodide Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- UJNOLBSYLSYIBM-NOOOWODRSA-N [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2S)-2-hydroxypropanoate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)[C@H](C)O UJNOLBSYLSYIBM-NOOOWODRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000001519 tissues Anatomy 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
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
- C07C69/68—Lactic acid esters
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 266120 KLASSE 12 o. GRUPPE- M 266120 CLASS 12 or GROUP
Verfahren zur Darstellung von Alkylmilchsäureestern.Process for the preparation of alkyl lactic acid esters.
Patentiert im Deutschen Reiche vom 3. Januar 1913 ab.Patented in the German Empire on January 3, 1913.
Bei der Alkylierung von Milchsäureestern mit Hilfe von Halogenalkylen und Ag2 O, wie sie z. B. von Purdie und Irvine (Journ. Chem. Soc. 75, S. 486) beschrieben ist, werden dann schlechte Ausbeuten erhalten, wenn der Alkoholrest des Esters nicht mit dem des Alkylierungsmittels identisch ist, oder andernfalls, wenn nicht ein großer Überschuß von Alkylierungsmitteln und Ag2O verwendet wird.In the alkylation of lactic acid esters with the help of haloalkylenes and Ag 2 O, as they are, for. B. by Purdie and Irvine (Journ. Chem. Soc. 75, p. 486), poor yields are obtained when the alcohol residue of the ester is not identical to that of the alkylating agent, or otherwise, if not a large excess of Alkylating agents and Ag 2 O is used.
Es wurde nun die Beobachtung gemacht, daß bei Zusatz eines wasserbindenden Mittels zum Reaktionsgemisch quantitative Ausbeuten reiner Produkte bei Anwendung der theoretisch zum Umsatz notwendigen Menge von Ag2O und Alkylhaloid erhalten werden. Unter anderem gelang auf diesem Wege die erstmalige Darstellung reiner . Alkylmilchsäurementholester, die sonst nur schwierig zugänglich sind.It has now been observed that when a water-binding agent is added to the reaction mixture, quantitative yields of pure products are obtained using the amount of Ag 2 O and alkyl halide theoretically required for conversion. In this way, among other things, the first presentation of purer succeeded. Alkyl lactic acid elmenthol esters, which are otherwise difficult to access.
I. 59 g Milchsäureäthylester, 74 g Methyljodid und 20 g wasserfreies Natriumsulfat werden unter Turbinieren und Kühlen allmählich mit 60 g Ag2O versetzt; nach 4 stündigem Rühren wird vom AgJ und Na2SO 4 abfiltriert und der -Methomilchsäureäthylester von etwas überschüssigem Methyljodid und Spuren unveränderten Milchsäureäthylesters durch Destillation befreit.I. 59 g of ethyl lactate, 74 g of methyl iodide and 20 g of anhydrous sodium sulfate are gradually admixed with 60 g of Ag 2 O while cooling and cooling; After stirring for 4 hours, AgI and Na 2 SO 4 are filtered off and the methyl lactate is freed from a little excess methyl iodide and traces of unchanged ethyl lactate by distillation.
II. 23 g Milchsäurementhylester werden in 20 g Äthyljodid und 20 g Äther gelöst und mit 12 g Ag2O und 20 g wasserfreiem CuSO i 10 Stunden gekocht. Aufgearbeitet wird wie bei Beispiel I; der Äthomilchsäurementhylester siedet unter 10 mm bei 133 °.II. 23 g menthyl lactate are dissolved in 20 g of ethyl iodide and 20 g of ether and boiled for 10 hours 12 g of Ag 2 O and 20 g of anhydrous CuSO i. Working up is as in Example I; the menthyl etholactate boils below 10 mm at 133 °.
III. 23 g Milchsäurementhylester, 15 g Methyljodid, 20 g Äther, 13 g Ag2 0, 12 g CuSO4 werden wie im Beispiel II behandelt. Der Methomilchsäurementholestersiedet unter 10mm bei etwa 130 °.III. 23 g of tungsten lactate, 15 g of methyl iodide, 20 g of ether, 13 g of Ag 2 0, 12 g of CuSO 4 are treated as in Example II. The metholactic acid holester boils below 10mm at about 130 °.
Die erhaltenen Produkte haben teils selbst pharmazeutisch wertvolle Eigenschaften — so werden die Mentholester von den Gewebsäften leicht verseift — teils sollen sie als pharmazeutische Zwischenprodukte dienen.Some of the products obtained have pharmaceutically valuable properties themselves - see above the menthol esters are easily saponified by the tissue juices - sometimes they are supposed to be pharmaceutical Serve intermediates.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE266120C true DE266120C (en) |
Family
ID=523289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT266120D Active DE266120C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE266120C (en) |
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0
- DE DENDAT266120D patent/DE266120C/de active Active
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