PL432400A1 - (EZ, 2 EZ) -3, 7-dimethyl-N- (oxiran-2 (RS) -ylmethoxy) octa-2,6-diene-1-imine and its preparation - Google Patents
(EZ, 2 EZ) -3, 7-dimethyl-N- (oxiran-2 (RS) -ylmethoxy) octa-2,6-diene-1-imine and its preparationInfo
- Publication number
- PL432400A1 PL432400A1 PL432400A PL43240019A PL432400A1 PL 432400 A1 PL432400 A1 PL 432400A1 PL 432400 A PL432400 A PL 432400A PL 43240019 A PL43240019 A PL 43240019A PL 432400 A1 PL432400 A1 PL 432400A1
- Authority
- PL
- Poland
- Prior art keywords
- oxiran
- ylmethoxy
- octa
- imine
- diene
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- VNITWECRGKELIE-UHFFFAOYSA-N CC(C)=CCCC(C)=CC=NOCC1OC1 Chemical compound CC(C)=CCCC(C)=CC=NOCC1OC1 VNITWECRGKELIE-UHFFFAOYSA-N 0.000 abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- LXFKDMGMYAHNAQ-AMMQDNIMSA-N (ne)-n-[(2e)-3,7-dimethylocta-2,6-dienylidene]hydroxylamine Chemical compound CC(C)=CCC\C(C)=C\C=N\O LXFKDMGMYAHNAQ-AMMQDNIMSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 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
- 239000012043 crude product Substances 0.000 abstract 1
- 239000002274 desiccant Substances 0.000 abstract 1
- 239000012153 distilled water Substances 0.000 abstract 1
- 238000004508 fractional distillation Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000012044 organic layer Substances 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003505 terpenes Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Abstract
Wynalazek ujawnia (EZ, 2EZ)-3,7-dimetylo-N-(oksiran-2(RS)-ylometoksy)okta-2,6-dien-1-imina o wzorze 1 mającą zastosowanie jako środek zapachowy. Wynalazek ujawnia również sposób wytwarzania (EZ, 2EZ)-3,7-dimetylo-N-(oksiran-2(RS)-ylometoksy)okta-2,6-dien-1-iminy będącą terpenoidową pochodną o wzorze 1 polegający na tym, że oksym 3,7-dimetylookta-2,6-dienalu poddaje się reakcji O-alkilowania epichlorohydryną, przy czym reakcję prowadzi się w kolbie na mieszadle magnetycznym w obecności dimetylosulfotlenku jako rozpuszczalnika przez 24 godziny, a po zakończeniu reakcji rozcieńcza się mieszaninę reakcyjną wodą destylowaną i umieszcza się całość w rozdzielaczu, następnie mieszaninę ekstrahuje się trzykrotnie heksanem i tak połączone warstwy organiczne suszy się bezwodnym siarczanem magnezu, następnie odfiltrowuje się środek suszący i odparowuje rozpuszczalniki, a surowy produkt oczyszcza się za pomocą frakcyjnej destylacji próżniowej.The invention discloses (EZ, 2EZ) -3,7-dimethyl-N- (oxiran-2 (RS) -ylmethoxy) octa-2,6-diene-1-imine of formula 1 for use as a perfume. The invention also discloses a process for the preparation of (EZ, 2EZ) -3,7-dimethyl-N- (oxiran-2 (RS) -ylmethoxy) octa-2,6-diene-1-imine, a terpenoid derivative of formula 1 which is that 3,7-dimethylocta-2,6-dienal oxime is subjected to an O-alkylation reaction with epichlorohydrin, the reaction being carried out in a flask on a magnetic stirrer in the presence of dimethylsulfoxide as a solvent for 24 hours, and after the reaction is completed, the reaction mixture is diluted with distilled water and place it in a separating funnel, then the mixture is extracted three times with hexane and the combined organic layers are dried over anhydrous magnesium sulfate, then the drying agent is filtered off and the solvents are evaporated, and the crude product is purified by vacuum fractional distillation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL432400A PL241187B1 (en) | 2019-12-24 | 2019-12-24 | (EZ, 2 EZ) -3, 7-dimethyl-N- (oxiran-2 (RS) -ylmethoxy) octa-2,6-diene-1-imine and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL432400A PL241187B1 (en) | 2019-12-24 | 2019-12-24 | (EZ, 2 EZ) -3, 7-dimethyl-N- (oxiran-2 (RS) -ylmethoxy) octa-2,6-diene-1-imine and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL432400A1 true PL432400A1 (en) | 2021-06-28 |
| PL241187B1 PL241187B1 (en) | 2022-08-22 |
Family
ID=76547893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL432400A PL241187B1 (en) | 2019-12-24 | 2019-12-24 | (EZ, 2 EZ) -3, 7-dimethyl-N- (oxiran-2 (RS) -ylmethoxy) octa-2,6-diene-1-imine and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL241187B1 (en) |
-
2019
- 2019-12-24 PL PL432400A patent/PL241187B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL241187B1 (en) | 2022-08-22 |
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