AT39444B - Process for the preparation of the bromoisovaleric acid esters of borneol and isoborneol. - Google Patents
Process for the preparation of the bromoisovaleric acid esters of borneol and isoborneol.Info
- Publication number
- AT39444B AT39444B AT39444DA AT39444B AT 39444 B AT39444 B AT 39444B AT 39444D A AT39444D A AT 39444DA AT 39444 B AT39444 B AT 39444B
- Authority
- AT
- Austria
- Prior art keywords
- isoborneol
- borneol
- preparation
- acid esters
- bromoisovaleric acid
- Prior art date
Links
- DTGKSKDOIYIVQL-UHFFFAOYSA-N Borneol Chemical compound C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 title claims description 9
- UEBARDWJXBGYEJ-UHFFFAOYSA-N 2-bromo-3-methylbutanoic acid Chemical class CC(C)C(Br)C(O)=O UEBARDWJXBGYEJ-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 claims description 7
- -1 isoborneol ester Chemical class 0.000 claims description 6
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 5
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- DTGKSKDOIYIVQL-MRTMQBJTSA-N Isoborneol Natural products C1C[C@@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-MRTMQBJTSA-N 0.000 claims description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 3
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 claims description 3
- 229940116229 borneol Drugs 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 150000001637 borneol derivatives Chemical class 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
EMI1.1
Das Patent Nr. 39443 betrifft ein Verfahren zur Darstellung der Bromisovalerian- säureester von Borneol und Isoborneol. Es besteht darin, dass man Bromisovaleriansäure-
EMI1.2
sationsmitteln zur Umsetzung bringt, oder Bromisovaleriansäure auf Kamphen bei Gegenwart von Kondensationsmitteln einwirken lässt.
Nach dem vorliegenden Zusatzpatent kann man zu den Bromisova) eriansäureestern der Borneole auch in der Weise gelangen, dass man den Borneol-bezw. Isoborneolester der Isovaleriansäure bromiert, und zwar mit oder ohne Bromüberträgern.
Beispiel : Zu 500 9 Isovaleriansäureborneolester lässt man 400 9 Brom zutropfen, während man auf dem Wasserbad so lange erhitzt, bis die Lösung farblos wird. Zur Bindung der Bromwasserstoffsäure kann man eventuell Natriumkarbonat zusetzen. Hierauf destilliert man im Vakuum. Zur besseren Ausbeute können auch geeignete Bromüberträger zugefügt werden.
Ersetzt man den Isovaleriansäureborneolester durch den Isovaleriansäureisoborneolester, so erhält man die entsprechende Bromverbindung.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
EMI1.1
Patent No. 39443 relates to a process for the preparation of the bromoisovaleric acid esters of borneol and isoborneol. It consists of bromoisovaleric acid
EMI1.2
brings sationsmittel to the implementation, or bromoisovaleric acid can act on camphene in the presence of condensation agents.
According to the present additional patent, the Bromisova) erian acid esters of the borneols can also be obtained in such a way that the borneol or. Isoborneol ester of isovaleric acid is brominated, with or without bromine carriers.
Example: 400 9 bromine are added dropwise to 500 9 isovaleric acid borneol esters, while heating is carried out on a water bath until the solution becomes colorless. Sodium carbonate can optionally be added to bind the hydrobromic acid. It is then distilled in vacuo. Suitable bromine carriers can also be added to improve the yield.
If the isovaleric acid borneol ester is replaced by the isovaleric acid isoborneol ester, the corresponding bromine compound is obtained.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1908205264D DE205264C (en) | 1908-01-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT39444B true AT39444B (en) | 1909-10-25 |
Family
ID=5786268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT39444D AT39444B (en) | 1908-01-20 | 1908-07-06 | Process for the preparation of the bromoisovaleric acid esters of borneol and isoborneol. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT39444B (en) |
-
1908
- 1908-07-06 AT AT39444D patent/AT39444B/en active
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