PL405307A1 - (-)-O-isoamyloximinofenchane and its preparation method - Google Patents
(-)-O-isoamyloximinofenchane and its preparation methodInfo
- Publication number
- PL405307A1 PL405307A1 PL405307A PL40530713A PL405307A1 PL 405307 A1 PL405307 A1 PL 405307A1 PL 405307 A PL405307 A PL 405307A PL 40530713 A PL40530713 A PL 40530713A PL 405307 A1 PL405307 A1 PL 405307A1
- Authority
- PL
- Poland
- Prior art keywords
- reaction
- formula
- isoamyloxyiminofenchane
- isoamyloxyiminofenchan
- fenchone
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 239000012044 organic layer Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- LHXDLQBQYFFVNW-OIBJUYFYSA-N (-)-Fenchone Chemical compound C1C[C@@]2(C)C(=O)C(C)(C)[C@@H]1C2 LHXDLQBQYFFVNW-OIBJUYFYSA-N 0.000 abstract 1
- 229930006729 (1R,4S)-fenchone Natural products 0.000 abstract 1
- CZHLPWNZCJEPJB-UHFFFAOYSA-N 1-chloro-3-methylbutane Chemical compound CC(C)CCCl CZHLPWNZCJEPJB-UHFFFAOYSA-N 0.000 abstract 1
- 235000011293 Brassica napus Nutrition 0.000 abstract 1
- 240000008100 Brassica rapa Species 0.000 abstract 1
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 abstract 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract 1
- 238000010934 O-alkylation reaction Methods 0.000 abstract 1
- 235000016954 Ribes hudsonianum Nutrition 0.000 abstract 1
- 240000001890 Ribes hudsonianum Species 0.000 abstract 1
- 235000001466 Ribes nigrum Nutrition 0.000 abstract 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 1
- LHXDLQBQYFFVNW-UHFFFAOYSA-N alpha-fenchone Natural products C1CC2(C)C(=O)C(C)(C)C1C2 LHXDLQBQYFFVNW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000002274 desiccant Substances 0.000 abstract 1
- 239000003205 fragrance Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
Wynalazek dotyczy (-)-O-izoamyloksyiminofenchan o wzorze 1 znajdującego zastosowanie jako związek zapachowy scharakteryzowany jako rzepa i czarna porzeczka. Wynalazek obejmuje również sposób wytwarzania (-)-O-izoamyloksyiminofenchanu o wzorze 1 polegający na tym, że sól sodową oksymu (-)-fenchonu poddaje się reakcji O-alkilowania chlorkiem izoamylu, przy czym reakcję prowadzi się pod refluksem w obecności toluenu jako rozpuszczalnika przez 24 godziny. Następnie po zakończeniu reakcji do kolby z mieszaniną reakcyjną wlewa się nasycony roztwór wodorowęglanu sodu, całość umieszcza się w rozdzielaczu, oddziela się warstwę organiczną od wodnej, a tę ostatnią ekstrahuje się dwukrotnie eterem dietylowym i połączone warstwy organiczne suszy się nad bezwodnym siarczanem magnezu, odfiltrowuje się środek suszący i odparowuje rozpuszczalniki.The invention relates to (-) - O-isoamyloxyiminofenchan of the formula I which is used as a fragrance compound characterized as turnip and black currant. The invention also includes a process for producing (-) - O-isoamyloxyiminofenchane of formula 1, wherein the sodium salt of (-) - fenchone oxime is subjected to an O-alkylation reaction with isoamyl chloride, the reaction being carried out under reflux in the presence of toluene as a solvent by 24 hours. Then, after completion of the reaction, a saturated sodium bicarbonate solution is poured into the reaction flask, the whole is placed in a separatory funnel, the organic layer is separated from the aqueous one, the latter is extracted twice with diethyl ether and the combined organic layers are dried over anhydrous magnesium sulfate, filtered desiccant and evaporates solvents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL405307A PL221469B1 (en) | 2013-09-11 | 2013-09-11 | (-)-O-isoamyloximinofenchane and its preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL405307A PL221469B1 (en) | 2013-09-11 | 2013-09-11 | (-)-O-isoamyloximinofenchane and its preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL405307A1 true PL405307A1 (en) | 2014-04-14 |
| PL221469B1 PL221469B1 (en) | 2016-04-29 |
Family
ID=50442235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL405307A PL221469B1 (en) | 2013-09-11 | 2013-09-11 | (-)-O-isoamyloximinofenchane and its preparation method |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL221469B1 (en) |
-
2013
- 2013-09-11 PL PL405307A patent/PL221469B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL221469B1 (en) | 2016-04-29 |
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