PL212514B1 - New R-(-)-(5,5-dimethylcyclohex-2-en-1-yl) acetaldehyde and the process for preparation thereof - Google Patents
New R-(-)-(5,5-dimethylcyclohex-2-en-1-yl) acetaldehyde and the process for preparation thereofInfo
- Publication number
- PL212514B1 PL212514B1 PL392178A PL39217810A PL212514B1 PL 212514 B1 PL212514 B1 PL 212514B1 PL 392178 A PL392178 A PL 392178A PL 39217810 A PL39217810 A PL 39217810A PL 212514 B1 PL212514 B1 PL 212514B1
- Authority
- PL
- Poland
- Prior art keywords
- dimethylcyclohex
- new
- preparation
- acetaldehyde
- aldehyde
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- ZWRDLPVBXCLSIP-VIFPVBQESA-N 2-[(1R)-5,5-dimethylcyclohex-2-en-1-yl]acetaldehyde Chemical compound CC1(C)CC=C[C@@H](CC=O)C1 ZWRDLPVBXCLSIP-VIFPVBQESA-N 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 8
- 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 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 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
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Przedmiotem wynalazku jest nowy aldehyd R-(-)-(5,5-dimetylocykloheks-2-en-1-ylo)octowy przedstawiony na rysunku i sposób jego otrzymywania.The subject of the invention is the new R - (-) - (5,5-dimethylcyclohex-2-en-1-yl) acetic aldehyde 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 perfume and food industries.
W dostę pnej literaturze nie znaleziono publikacji o otrzymywaniu aldehydu R-(-)-(5,5-dimetylocykloheks-2-en-1-ylo)octowego.In the available literature, no publications on the preparation of R - (-) - (5,5-dimethylcyclohex-2-en-1-yl) acetic aldehyde were found.
Istotą wynalazku jest nowy aldehyd R-(-)-(5,5-dimetylocykloheks-2-en-1-ylo)octowy przedstawiony na rysunku.The essence of the invention is the new R - (-) - (5,5-dimethylcyclohex-2-en-1-yl) acetic aldehyde shown in the drawing.
Istotą wynalazku jest również sposób otrzymywania nowego aldehydu R-(-)-(5,5-dimetylocykloheks-2-en-1-ylo)octowego.The essence of the invention is also the method of obtaining the new R - (-) - (5,5-dimethylcyclohex-2-en-1-yl) acetic aldehyde.
Sposób, otrzymania nowego aldehydu polega na tym, że znany R-(-)-2-(5,5-dimetylocykloheks-2-en-1-ylo)etanol (K. Wińska, K. Grudniewska, A. Chojnacka, A. Białońska, C. Wawrzeńczyk; Tetrahedron:Asymmetry 2010, 21,670-678) utlenia się kompleksem CrO3Py w chlorku metylenu, otrzymując aldehyd R-(-)-(5,5-dimetylocykloheks-2-en-1-ylo)octowy.The method of obtaining a new aldehyde consists in the fact that 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) is oxidized with a CrO 3 Py complex in methylene chloride to give R - (-) - (5,5-dimethylcyclohex-2-en-1-yl) acetic aldehyde.
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 d 3 Example 3
Do chłodzonej wodą z lodem mieszaniny tlenku chromu (VI) (0.8 g, 8 mmol) i pirydyny (4 cm3, 52 mmol) w bezwodnym chlorku metylenu wkrapla się R-(-)-2-(5,5-dimetylocykloheks-2-en-1-ylo)etanol (0.20 g, 1.19 mmol) rozpuszczony w chlorku metylenu (15 cm3). Całość miesza się następnie w temperaturze pokojowej. Po zakończeniu reakcji (TLC) mieszaninę reakcyjną przesącza się przez Florisil używając heksanu (50 cm3) jako eluentu. Otrzymany roztwór przemywa się wodą, 5% roztworem CuSO4, nasyconym roztworem Na2CO3, solanką i suszy się bezwodnym MgSO4. Surowy produkt oczyszcza się za pomocą chromatografii kolumnowej (żel krzemionkowy, heksan : aceton, 9:1). Uzyskuje się 0.13 g (wydajność 66%) czystego aldehydu o zapachu średnio intensywnym, owocowokwiatowym.To the ice-water chilled mixture of chromium oxide (VI) (0.8 g, 8 mmol) and pyridine (4 cm 3, 52 mmol) in anhydrous methylene chloride is added dropwise to R - (-) - 2- (5,5-dimethyl-cyclohex-2 -en-1-yl) ethanol (0.20 g, 1.19 mmol) dissolved in methylene chloride (15 cm 3 ). The mixture is then stirred at room temperature. After completion of the reaction (TLC), the reaction mixture is filtered over Florisil using hexane (50 cm 3 ) as the eluent. The resulting solution was washed with water, 5% CuSO4 solution, saturated Na2CO3 solution, brine and dried with anhydrous MgSO4. The crude product is purified by column chromatography (silica gel, hexane: acetone, 9: 1). The obtained is 0.13 g (yield 66%) of pure aldehyde with a moderately intense, fruity-floral odor.
Otrzymuje się R-(-)-aldehyd, który charakteryzuje się następującymi właściwościami fizycznymi i spektroskopowymi:The R - (-) - aldehyde is obtained, which has the following physical and spectroscopic properties:
[α] D 23 = -15.8 (c = 0.73, CHCl3); nD 20 = 1.4735; 1H NMR (300 MHz, CDCl3) δ: 0.92 i 0.94 ( dwa s, 6H, (CH3)2C<)), 1.05 (dd, J = 12,7 i 12.1 Hz, 1H, jeden z CH2-6), 1.48 (dd, J = 12.7 i 5.5 Hz, 1H, jeden z CH2-6), 1.71 i 1.85 (dm, J = 17.7 Hz, 2H, CH2-4), 2.36 i 2.44 (dwa ddd, J = 16.4, 7.3 i 1.9 Hz, m, 2H, CH2-7), 2.70 (m, 1H, H-1), 4.70 (dm, J = 10.0 Hz, 1H, H-2), 5.66 (ddt, J = 10.0, 5.4 i 2.3 Hz, 1H, H-3), 9.79 ( t, J = 2.0 Hz, 1H, -C(O)H); IR (film, cm-1): 3019 (m), 2951 (s), 1726 (s).[α] D 23 = -15.8 (c = 0.73, CHCl3); n D 20 = 1.4735; 1 H NMR (300 MHz, CDCl3) δ: 0.92 and 0.94 (two s, 6H, (CH3) 2C <)), 1.05 (dd, J = 12.7 and 12.1 Hz, 1H, one CH2-6) 1.48 (dd, J = 12.7 and 5.5 Hz, 1H, one of CH2-6), 1.71 and 1.85 (dm, J = 17.7 Hz, 2H, CH2-4), 2.36 and 2.44 (two ddd, J = 16.4, 7.3 and 1.9 Hz, m, 2H, CH2-7), 2.70 (m, 1H, H-1), 4.70 (dm, J = 10.0 Hz, 1H, H-2), 5.66 (ddt, J = 10.0, 5.4 and 2.3 Hz, 1H, H-3), 9.79 (t, J = 2.0 Hz, 1H, -C (O) H); IR (film, cm -1 ): 3019 (m), 2951 (s), 1726 (s).
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL392178A PL212514B1 (en) | 2010-08-19 | 2010-08-19 | New R-(-)-(5,5-dimethylcyclohex-2-en-1-yl) acetaldehyde and the process for preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL392178A PL212514B1 (en) | 2010-08-19 | 2010-08-19 | New R-(-)-(5,5-dimethylcyclohex-2-en-1-yl) acetaldehyde and the process for preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL392178A1 PL392178A1 (en) | 2011-02-14 |
| PL212514B1 true PL212514B1 (en) | 2012-10-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL392178A PL212514B1 (en) | 2010-08-19 | 2010-08-19 | New R-(-)-(5,5-dimethylcyclohex-2-en-1-yl) acetaldehyde and the process for preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL212514B1 (en) |
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2010
- 2010-08-19 PL PL392178A patent/PL212514B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL392178A1 (en) | 2011-02-14 |
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| LICE | Declarations of willingness to grant licence |
Effective date: 20120615 |
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| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20130819 |