PL214896B1 - New R-(-)-2-(5,5-dimethylcyclohex-2-en-1-yl) ethyl acetate and the process for preparation thereof - Google Patents
New R-(-)-2-(5,5-dimethylcyclohex-2-en-1-yl) ethyl acetate and the process for preparation thereofInfo
- Publication number
- PL214896B1 PL214896B1 PL392173A PL39217310A PL214896B1 PL 214896 B1 PL214896 B1 PL 214896B1 PL 392173 A PL392173 A PL 392173A PL 39217310 A PL39217310 A PL 39217310A PL 214896 B1 PL214896 B1 PL 214896B1
- Authority
- PL
- Poland
- Prior art keywords
- dimethylcyclohex
- new
- ethyl acetate
- preparation
- diethyl ether
- Prior art date
Links
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 title claims description 14
- -1 R-(-)-2-(5,5-dimethylcyclohex-2-en-1-yl) ethyl Chemical group 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012346 acetyl chloride Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- JWGVNYKCXJQRDU-VIFPVBQESA-N 2-[(1R)-5,5-dimethylcyclohex-2-en-1-yl]ethanol Chemical compound CC1(C)CC=C[C@@H](CCO)C1 JWGVNYKCXJQRDU-VIFPVBQESA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest nowy octan R-(-)-2-(5,5-dimetylocykloheks-2-en-1-ylo)etylu przedstawiony na rysunku i sposób jego otrzymywania.The subject of the invention is the new R - (-) - 2- (5,5-dimethylcyclohex-2-en-1-yl) ethyl acetate shown in the drawing and the method of its preparation.
Związek ten charakteryzuje się wartościowym zapachem i może znaleźć zastosowanie, jako składnik kompozycji zapachowych, w przemyśle perfumeryjnym oraz spożywczym.This compound is characterized by a valuable scent and can be used as an ingredient in fragrance compositions in the perfumery and food industries.
W dostępnej literaturze nie znaleziono publikacji o otrzymywaniu octanów 2-(5,5-dimetylocykloheks-2-en-1-ylo)etylu.No publications on the preparation of 2- (5,5-dimethylcyclohex-2-en-1-yl) ethyl acetates were found in the available literature.
Istotą wynalazku jest nowy octan R-(-)-2-(5,5-dimetylocykloheks-2-en-1-ylo)etylu przedstawiony na rysunku.The essence of the invention is the new R - (-) - 2- (5,5-dimethylcyclohex-2-en-1-yl) ethyl acetate shown in the drawing.
Istotą wynalazku jest również sposób otrzymywania nowego octanu R-(-)-2-(5,5-dimetylocykloheks-2-en-1-ylo)etylu.The essence of the invention is also the method of obtaining the new R - (-) - 2- (5,5-dimethylcyclohex-2-en-1-yl) ethyl acetate.
Sposób otrzymania nowego octanu polega na tym, że w reakcji znanego R-(-)-2-(5,5-dimetylocykloheks-2-en-1-ylo)etanolu (K. Wińska, K. Grudniewska, A. Chojnacka, A. Białońska, C. Wawrzeńczyk; Tetrahedron: Asymmetry 2010, 21, 670-678) z chlorkiem acetylu, w obecności pirydyny i suchego eteru dietylowego, otrzymuje się octan R-(-)-2-(5,5-dimetylocykloheks-2-en-1-ylo)etylu przedstawiony na rysunku.The method of obtaining a new acetate consists in the fact that in the reaction of the known R - (-) - 2- (5,5-dimethylcyclohex-2-en-1-yl) ethanol (K. Wińska, K. Grudniewska, A. Chojnacka, A Białońska, C. Wawrzeńczyk; Tetrahedron: Asymmetry 2010, 21, 670-678) with acetyl chloride, in the presence of pyridine and dry diethyl ether, the R - (-) - 2- (5,5-dimethylcyclohex-2-) acetate is obtained. en-1-yl) ethyl shown in the figure.
Sposób według wynalazku objaśniony jest w przykładach wykonania.The method according to the invention is explained in the working examples.
P r z y k ł a dP r z k ł a d
Do mieszaniny alkoholu (0,10 g, 0,7 mmol) i bezwodnej pirydyny (0,11 g, 1,5 mmol) w eterze 3 dietylowym (10 cm3) wkrapla się chlorek acetylu (0,05 g, 0,8 mmol) rozpuszczony w bezwodnym 3 eterze dietylowym (5 cm3), a następnie mieszaninę reakcyjną rozcieńcza się eterem dietylowym 3 (100 cm3) po 7 godzinach mieszania. Warstwę organiczną wytrząsa się z roztworem HCl i po oddzieleniu warstwy eterowej, fazę wodną ekstrahuje się dodatkowo eterem dietylowym (3 x 25 cm3). Połączone ekstrakty eterowe przemywa się rozcieńczonym (10%) roztworem H2SO4, nasyconym roztworem NaHCO3, solanką, a następnie suszy się bezwodnym MgSO4 i oczyszcza za pomocą chromatografii kolumnowej (żel krzemionkowy, eluent heksan:aceton, 9:1) uzyskując 0,11 g (wydajność 86%) octanu R-(-)-2-(5,5-dimetylocykloheks-2-en-1-ylo)etylu o zapachu średnio-intensywnym, owocowym z nutą jabłkową.To a mixture of the alcohol (0.10 g, 0.7 mmol) and anhydrous pyridine (0.11 g, 1.5 mmol) in diethyl ether 3 (10 cm 3) was added dropwise acetyl chloride (0.05 g, 0.8 mmol) dissolved in anhydrous diethyl ether 3 (5 cm 3) and then the reaction mixture was diluted with diethyl ether 3 (100 cm 3) after 7 hours of stirring. The organic layer is shaken with HCl solution and, after separation of the ether layer, the aqueous phase is further extracted with diethyl ether (3 x 25 cm 3 ). The combined ether extracts were washed with dilute (10%) H 2 SO 4, saturated NaHCO 3, brine then dried over anhydrous MgSO 4 and purified by column chromatography (silica gel, eluent hexane: acetone, 9: 1) to yield 0.11 g ( yield 86%) of R - (-) - 2- (5,5-dimethylcyclohex-2-en-1-yl) ethyl acetate with a medium-intense fruity aroma with a hint of apple.
Otrzymany octan charakteryzuje się następującymi właściwościami fizycznymi i spektroskopowymi:The obtained acetate has the following physical and spectroscopic properties:
[a]23D = -32,3 (c = 0,69, CHCI3);[a] 23 D = -32.3 (c = 0.69, CHCl 3);
N20D = 1,4559;N 20 D = 1.4559;
1H NMR (600 MHz, CDCl3) δ: 0,81 i 0,94 ( dwa s, 6H, (CH3)2C<)), 1,02 (dd, J = 12,7 i 12,0 Hz, 1H, jeden z CH2-6), 1,44 (dd, J = 12,7 i 5,5 Hz, 1H, jeden z CH2-6), 1,57 (m, 2H, jeden z CH2-7), 1,66 i 1,74 (dwa m, 2H, jeden z CH2-7 i jeden z CH2-4), 1,83 (m, 1H, jeden z CH2-4), 2,05 (s, 3H, -C(O)CH3), 2,21 (m, 1H, H-1), 4,12 i 4,15 (dwa dt, J = 11,1 i 7,0 Hz, 2H, -CH2CH2O-), 5,50 (dm, J = 10,0 Hz, 1H, H-2), 5,61 (m, 1H, H-3); 1 H NMR (600 MHz, CDCl3) δ: 0.81 and 0.94 (two s, 6H, (CH3) 2C <)), 1.02 (dd, J = 12.7 and 12.0 Hz, 1 H , one of CH2-6), 1.44 (dd, J = 12.7 and 5.5 Hz, 1H, one of CH2-6), 1.57 (m, 2H, one of CH2-7), 1 , 66 and 1.74 (two m, 2H, one from CH2-7 and one from CH2-4), 1.83 (m, 1H, one from CH2-4), 2.05 (s, 3H, -C (O) CH3), 2.21 (m, 1H, H-1), 4.12 and 4.15 (two dt, J = 11.1 and 7.0 Hz, 2H, -CH2CH2O-), 5, 50 (dm, J = 10.0 Hz, 1H, H -2), 5.61 (m, 1H, H-3);
IR (film, cm-1): 3013 (w), 2951 (s), 1743 (s), 1240 (s),1032 (m).IR (film, cm -1 ): 3013 (i), 2951 (s), 1743 (s), 1240 (s), 1032 (m).
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL392173A PL214896B1 (en) | 2010-08-19 | 2010-08-19 | New R-(-)-2-(5,5-dimethylcyclohex-2-en-1-yl) ethyl acetate and the process for preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL392173A PL214896B1 (en) | 2010-08-19 | 2010-08-19 | New R-(-)-2-(5,5-dimethylcyclohex-2-en-1-yl) ethyl acetate and the process for preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL392173A1 PL392173A1 (en) | 2011-02-14 |
| PL214896B1 true PL214896B1 (en) | 2013-09-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL392173A PL214896B1 (en) | 2010-08-19 | 2010-08-19 | New R-(-)-2-(5,5-dimethylcyclohex-2-en-1-yl) ethyl acetate and the process for preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL214896B1 (en) |
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2010
- 2010-08-19 PL PL392173A patent/PL214896B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL392173A1 (en) | 2011-02-14 |
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| LICE | Declarations of willingness to grant licence |
Effective date: 20130425 |
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| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20130819 |