PL110254B2 - Method of producing new derivative of trimethylcyclopentene - Google Patents
Method of producing new derivative of trimethylcyclopentene Download PDFInfo
- Publication number
- PL110254B2 PL110254B2 PL20897078A PL20897078A PL110254B2 PL 110254 B2 PL110254 B2 PL 110254B2 PL 20897078 A PL20897078 A PL 20897078A PL 20897078 A PL20897078 A PL 20897078A PL 110254 B2 PL110254 B2 PL 110254B2
- Authority
- PL
- Poland
- Prior art keywords
- trimethylcyclopentene
- producing new
- new derivative
- ylacetaldehyde
- derivative
- Prior art date
Links
- YNEQKUWRFVQFPF-UHFFFAOYSA-N 1,2,3-trimethylcyclopentene Chemical class CC1CCC(C)=C1C YNEQKUWRFVQFPF-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- AIZSHOZHOLKAGD-UHFFFAOYSA-N 2-(1,2,2-trimethylcyclopent-3-en-1-yl)acetaldehyde Chemical compound CC1(C)C=CCC1(C)CC=O AIZSHOZHOLKAGD-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000003747 Grignard reaction Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- -1 trimethyl cyclopenten-3-ylacetaldehyde derivative Chemical class 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 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
Landscapes
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania nowej pochodnej trójmetylocykiopentenu, o wzorze przedstawionym na rysunku, znajdujacej zastosowanie jako skladnik kompozycji perfumeryjnych.Istota wynalazku polega na tym, ze 2,2,3-trójmetylocyklopenten-3-yloacetaldehyd poddaje sie reakcji Grig- narda z halogenkiem allilomagnezowym.Nowa pochodna trójmetylocykiopentenu, wytworzona sposobem wedlug wynalazku, zarówno w postaci racemicznej, jak i optycznie czynnej ma trwaly i przyjemny zapach kwiatowy. Surowiec w postaci 2,2,3-trójme- tylocyklopenten-3-yloacetaldehydu jest zwiazkiem latwo dostepnym, wytwarzanym z duzymi wydajnosciami z kamfory albo alfa-pinenu.Przedmiot wynalazku jest objasniony w przykladzie wytwarzania nowej pochodnej trójmetylocykiopen¬ tenu, l-/2,2,3-trójmetylocyklopenten-3-ylo/penten-4-olu-2, o wzorze przedstawionym na rysunku.Przyklad. Do roztworu bromku allilomagnezowego, otrzymanego z 21,4 g (0,88 mola) magnezu i 106,5 g (0,88 mola) bromku allilu, w 700 rnl eteru, wkrapla sie powoli, przy jednoczesnym mieszaniu, w temperaturze 20°C, roztwór 121,8 g (0,80 mola) 2,2,3-trójmetylocyklopenten-3-yloacetaldehydu w 100 ml eteru. Mieszanine pozostawia sie na 2 godziny w temperaturze 20°C, a nastepnie rozklada nasyconym roztworem chlorku amonowe¬ go, oddziela faze eterowa, ekstrahuje faze wodna eterem,a polaczone ekstrakty przemywa roztworem wodoro¬ weglanu sodu i suszy siarczanem sodowym. Surowy produkt destyluje sie pod obnizonym cisnieniem, otrzymujac 137 g bezbarwnego oleju, stanowiacego l-/2,2,3-trójmetylocyklopenten-3-ylo/penten-4-ol-2, o wlasnosciach po¬ danych w ponizszej tabeli.Zastrzezenie patentowe Sposób wytwarzania nowej pochodnej trójmetylocykiopentenu, o wzorze przedstawionym na rysunku, namienny tym, ze 2,2,3-trójmetylocyklopenten-3-yloacetaldehyd poddaje sie reakcji Grignarda z halo¬ genkiem allilomagnezowym. PL
Claims (1)
1. Zastrzezenie patentowe Sposób wytwarzania nowej pochodnej trójmetylocykiopentenu, o wzorze przedstawionym na rysunku, namienny tym, ze 2,2,3-trójmetylocyklopenten-3-yloacetaldehyd poddaje sie reakcji Grignarda z halo¬ genkiem allilomagnezowym. PL
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL20897078A PL110254B2 (en) | 1978-08-09 | 1978-08-09 | Method of producing new derivative of trimethylcyclopentene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL20897078A PL110254B2 (en) | 1978-08-09 | 1978-08-09 | Method of producing new derivative of trimethylcyclopentene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL208970A1 PL208970A1 (pl) | 1979-07-02 |
| PL110254B2 true PL110254B2 (en) | 1980-07-31 |
Family
ID=19991011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL20897078A PL110254B2 (en) | 1978-08-09 | 1978-08-09 | Method of producing new derivative of trimethylcyclopentene |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL110254B2 (pl) |
-
1978
- 1978-08-09 PL PL20897078A patent/PL110254B2/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL208970A1 (pl) | 1979-07-02 |
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