AT41807B - Process for the preparation of the menthol ester of α-monobromoisovaleric acid. - Google Patents
Process for the preparation of the menthol ester of α-monobromoisovaleric acid.Info
- Publication number
- AT41807B AT41807B AT41807DA AT41807B AT 41807 B AT41807 B AT 41807B AT 41807D A AT41807D A AT 41807DA AT 41807 B AT41807 B AT 41807B
- Authority
- AT
- Austria
- Prior art keywords
- acid
- preparation
- monobromoisovaleric
- menthol
- menthol ester
- Prior art date
Links
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 title claims description 8
- 229940041616 menthol Drugs 0.000 title claims description 8
- UEBARDWJXBGYEJ-UHFFFAOYSA-N 2-bromo-3-methylbutanoic acid Chemical compound CC(C)C(Br)C(O)=O UEBARDWJXBGYEJ-UHFFFAOYSA-N 0.000 title claims description 4
- -1 menthol ester Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 4
- MVYUMPZRKNBHOP-UHFFFAOYSA-N 2-bromo-3-methylbutanoyl chloride Chemical compound CC(C)C(Br)C(Cl)=O MVYUMPZRKNBHOP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung des Mentholesters der x-Monobromisovaleriansäure.
EMI1.1
α-Monobromisovaleriansäurechlorid mit Menthol erfolgt schon in der laälte die Esterbildung ; dieselbe kann durch Erwärmen auf dem Wasser ad beschleunigt und zu Ende geführt werden.
EMI1.2
100 g α-Monobromisovalerylchlorid werden nun mit 80 g Menthol gekuppelt. Es bildet sich der α-Monobromisovaleriansäurementholester in nahezu theoretischer Ausbeute.
Das sauer reagierende Produkt wird zunächst mit verdünnter Sodalösung neutralisiert,
EMI1.3
im Vakuum destilliert.
Der a-Monobromisovaleriansäurementholester ist eine klare, farblose, sirupdicke
EMI1.4
unlöslich in Wasser. Diese neue Verbindung ist ein äusserst wirksames Nervonberuhigungsmittel. Sie siedet unter Atmosphärendruck bei 205 bis 2080 C und destilliert bei 50 mm Druck zwischen 150 bis 1600 C.
Gegenüber dem bekannten Methylester der x-Bromisovaleriansäure (Vergl. Liebigs Annalen 267, 1892, Seite 119) sowie den bisher zu therapeutischen Zwecken verwendeten,
EMI1.5
hat der neue Mentholester der α-Bromisovaleriansäure den Vorteil einer viel intensivereu, therapeutischen Wirkung, denn letzterem kommt nicht nur die spezifisch beruhigende Wirkung der (X-Broinisovaleriansäure auf das Zentralnervensystem, sondern auch diejenige des Menthols zu.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of the menthol ester of x-monobromoisovaleric acid.
EMI1.1
α-Monobromisovaleric acid chloride with menthol takes place in the cold, the ester formation; it can be accelerated and brought to an end by heating on the water ad.
EMI1.2
100 g of α-monobromoisovaleryl chloride are now coupled with 80 g of menthol. The α-monobromoisovaleric acid holester is formed in almost theoretical yield.
The acidic reacting product is first neutralized with a dilute soda solution,
EMI1.3
distilled in vacuo.
The a-monobromisovalerian acid holester is a clear, colorless, thick syrup
EMI1.4
insoluble in water. This new compound is an extremely effective nerve relaxant. It boils under atmospheric pressure at 205 to 2080 C and distills at 50 mm pressure between 150 to 1600 C.
Compared to the known methyl ester of x-bromoisovaleric acid (cf. Liebigs Annalen 267, 1892, page 119) and those previously used for therapeutic purposes,
EMI1.5
The new menthol ester of α-bromisovaleric acid has the advantage of a much more intense therapeutic effect, because the latter has not only the specific calming effect of (X-broinisovaleric acid on the central nervous system, but also that of menthol.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT41807T | 1908-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT41807B true AT41807B (en) | 1910-04-11 |
Family
ID=3560711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT41807D AT41807B (en) | 1908-02-28 | 1908-02-28 | Process for the preparation of the menthol ester of α-monobromoisovaleric acid. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT41807B (en) |
-
1908
- 1908-02-28 AT AT41807D patent/AT41807B/en active
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