PL224657B1 - Derivative of 5,9-dimethyldec-8-en-2-ol - Google Patents
Derivative of 5,9-dimethyldec-8-en-2-olInfo
- Publication number
- PL224657B1 PL224657B1 PL408808A PL40880814A PL224657B1 PL 224657 B1 PL224657 B1 PL 224657B1 PL 408808 A PL408808 A PL 408808A PL 40880814 A PL40880814 A PL 40880814A PL 224657 B1 PL224657 B1 PL 224657B1
- Authority
- PL
- Poland
- Prior art keywords
- dimethyldec
- derivative
- catalyst
- formula
- hexane
- Prior art date
Links
- MCENRHROIIQWOJ-UHFFFAOYSA-N 5,9-dimethyldec-8-en-2-ol Chemical class CC(CCC(C)O)CCC=C(C)C MCENRHROIIQWOJ-UHFFFAOYSA-N 0.000 title claims description 7
- AQYFLSJAPBSIFY-UHFFFAOYSA-N CC(C)CCCC(CCC(C)O)C Chemical compound CC(C)CCCC(CCC(C)O)C AQYFLSJAPBSIFY-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 240000000560 Citrus x paradisi Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 241000207199 Citrus Species 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 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
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Seasonings (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest pochodna 5,9-dimetylodec-8-en-2-olu, która znajduje zastosowanie jako związek zapachowy o woni przypominającej woń grejpfruta.The present invention relates to a 5,9-dimethyldec-8-en-2-ol derivative, which finds use as a fragrance with an odor resembling that of grapefruit.
Z opisu patentowego US 7534460 B2 jest znany 2,4,8-trimetylonon-7-en-2-ol o wzorzeFrom US 7534460 B2 there is known 2,4,8-trimethylone-7-en-2-ol of the formula
Z opisu zgłoszenia patentowego P. 401957 jest znany acykliczny alkohol, który stanowi 5,9-dimetylodec-8-en-2-ol o wzorzeFrom the patent application P. 401957 there is known an acyclic alcohol which is 5,9-dimethyldec-8-en-2-ol of the formula
Przedmiotem wynalazku jest pochodna 5,9-dimetylodec-8-en-2-olu, którą stanowi acykliczny alkohol, 5,9-dimetylodekan-2-ol o wzorze 1The present invention relates to the 5,9-dimethyldec-8-en-2-ol derivative, which is an acyclic alcohol, 5,9-dimethyldecan-2-ol of the formula 1
charakteryzujący się grejpfrutowym, cytrusowym zapachem. Dane spektralne 5,9-dimetylodekan-2-olu, stanowiącego mieszaninę dwóch racematów w proporcji 1:1, są następujące:characterized by a grapefruit, citrus scent. The spectral data of 5,9-dimethyldecan-2-ol, a mixture of two racemates in the ratio of 1: 1, is as follows:
1H NMR (250 MHz, CDCl3) δ 3,84-3,68 (m, J = 6.2 Hz, 1H), 1,53 (dd, J = 13.2 Hz, 6,7 Hz, 1H), 1,48-1,34 (m, 3H), 1,34-1,24 (m, 4H), 1,22-1,02 (m, 4H), 1,19 (d, J = 6.2 Hz, 3H), 0,85 (d, J = 6.6 Hz, 9H). 1 H NMR (250 MHz, CDCl 3 ) δ 3.84-3.68 (m, J = 6.2 Hz, 1H), 1.53 (dd, J = 13.2 Hz, 6.7 Hz, 1H), 1, 48-1.34 (m, 3H), 1.34-1.24 (m, 4H), 1.22-1.02 (m, 4H), 1.19 (d, J = 6.2Hz, 3H) , 0.85 (d, J = 6.6 Hz, 9H).
13C NMR (63 MHz, CDCl3) δ 68,5 (d), 68,4 (d), 39,3 (t), 37,2 (t), 37,2 (t), 36,8 (t), 36,8 (t), 33,0 (t), 13 C NMR (63 MHz, CDCl 3 ) δ 68.5 (d), 68.4 (d), 39.3 (t), 37.2 (t), 37.2 (t), 36.8 ( t), 36.8 (t), 33.0 (t),
32,9 (t), 32,8 (d), 32,8 (d), 27,9 (d), 24,7 (t), 23,5 (q), 23,4 (q), 22,7 (q), 22,6 (q), 19,6 (q), 19,6 (q).32.9 (t), 32.8 (d), 32.8 (d), 27.9 (d), 24.7 (t), 23.5 (q), 23.4 (q), 22 , 7 (q), 22.6 (q), 19.6 (q), 19.6 (q).
MS (70 eV) m/z (%) 186 (M+,0), 168 (M+-18, 6), 45 (100), 57 (62), 56 (59), 55 (46), 70 (45), 71 (41), 69 (41), 43 (40), 83 (35), 126 (29).MS (70 eV) m / z (%) 186 (M + 0), 168 (M + - 18.6), 45 (100), 57 (62), 56 (59), 55 (46), 70 (45 ), 71 (41), 69 (41), 43 (40), 83 (35), 126 (29).
Związek według wynalazku znajduje zastosowanie w aromatach spożywczych i kompozycjach perfumeryjnych.The compound of the invention finds use in food flavors and perfumery compositions.
Sposób otrzymywania 5,9-dimetylodekan-2-olu o wzorze 1, polega na tym, że 5,9-dimetylodec-8-en-2-ol poddaje się katalitycznej redukcji wodorem pod ciśnieniem atmosferycznym w środowisku heksanu, stosując jako katalizator korzystnie pallad osadzony na węglu aktywnym w ilości 10% wagowych w stosunku do całej masy katalizatora. Redukcję prowadzi się do zaniku substratu. Po zakończeniu redukcji odsącza się katalizator, oddestylowuje rozpuszczalnik i surowy produkt oczyszcza się chromatograficznie na żelu krzemionkowym stosując jako eluent mieszaninę heksan/octan etylu o stosunku objętościowym 9:1.The method of preparation of 5,9-dimethyldecan-2-ol of formula 1 consists in that 5,9-dimethyldec-8-en-2-ol is subjected to catalytic reduction with hydrogen at atmospheric pressure in hexane medium, using preferably palladium as a catalyst. supported on activated carbon in an amount of 10% by weight with respect to the total weight of the catalyst. The reduction is carried out until the substrate disappears. After the reduction is complete, the catalyst is filtered off, the solvent is distilled off and the crude product is purified by chromatography on silica gel using a 9: 1 v / v hexane / ethyl acetate mixture as eluent.
PL 224 657 B1PL 224 657 B1
Przedmiot wynalazku ilustruje poniższy przykład.The following example illustrates the subject of the invention.
P r z y k ł a d.P r z k ł a d.
Przez roztwór 0,15 g (0,8 mmol) 5,9-dimetylodec-8-en-2-olu w heksanie, z dodatkiem 15 mg katalizatora w postaci palladu osadzonego na węglu aktywnym, zawierającego 10% wagowych palladu w stosunku do całej masy katalizatora, przepuszczano wodór pod ciśnieniem atmosferycznym, aż do stwierdzenia zaniku substratu metodą chromatografii gazowej. Po odsączeniu katalizatora i oddest ylowaniu rozpuszczalnika otrzymano surowy produkt o zadowalającej czystości (94% GC). Surowy produkt poddano dodatkowemu oczyszczeniu metodą chromatografii kolumnowej na żelu krzemionkowym z zastosowaniem układu fazy ruchomej heksan/octan etylu w proporcji 9:1.By a solution of 0.15 g (0.8 mmol) of 5,9-dimethyldec-8-en-2-ol in hexane, with the addition of 15 mg of palladium on activated carbon catalyst containing 10% by weight of palladium in relation to the total weight of the catalyst, hydrogen was passed at atmospheric pressure until no starting material was detected by gas chromatography. After filtering off the catalyst and distilling off the solvent, the crude product was obtained in sufficient purity (94% GC). The crude product was further purified by column chromatography on silica gel using a 9: 1 hexane / ethyl acetate mobile phase system.
Otrzymano 0,13 g czystego produktu (>98% GC).0.13 g of pure product (> 98% GC) was obtained.
Dane spektralne w pełni potwierdziły budowę otrzymanego produktu.Spectral data fully confirmed the structure of the obtained product.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL408808A PL224657B1 (en) | 2014-07-10 | 2014-07-10 | Derivative of 5,9-dimethyldec-8-en-2-ol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL408808A PL224657B1 (en) | 2014-07-10 | 2014-07-10 | Derivative of 5,9-dimethyldec-8-en-2-ol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL408808A1 PL408808A1 (en) | 2016-01-18 |
| PL224657B1 true PL224657B1 (en) | 2017-01-31 |
Family
ID=55072270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL408808A PL224657B1 (en) | 2014-07-10 | 2014-07-10 | Derivative of 5,9-dimethyldec-8-en-2-ol |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL224657B1 (en) |
-
2014
- 2014-07-10 PL PL408808A patent/PL224657B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL408808A1 (en) | 2016-01-18 |
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