PL137382B2 - Process for preparing novel 2-/5,5-dimethyl-2-cyclohexen-1-yl/ethanol - Google Patents
Process for preparing novel 2-/5,5-dimethyl-2-cyclohexen-1-yl/ethanol Download PDFInfo
- Publication number
- PL137382B2 PL137382B2 PL24563384A PL24563384A PL137382B2 PL 137382 B2 PL137382 B2 PL 137382B2 PL 24563384 A PL24563384 A PL 24563384A PL 24563384 A PL24563384 A PL 24563384A PL 137382 B2 PL137382 B2 PL 137382B2
- Authority
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- Poland
- Prior art keywords
- dimethyl
- cyclohexen
- ethanol
- preparing novel
- ethyl
- Prior art date
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- -1 Ethyl 2- (5,5-dimethyl-2-cyclohexene-1-yl) ethanol Chemical compound 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- JWGVNYKCXJQRDU-UHFFFAOYSA-N 2-(5,5-dimethylcyclohex-2-en-1-yl)ethanol Chemical compound CC1(C)CC=CC(CCO)C1 JWGVNYKCXJQRDU-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
- 235000016970 Fragaria moschata Nutrition 0.000 description 1
- 244000307700 Fragaria vesca Species 0.000 description 1
- 235000014828 Fragaria vesca ssp. americana Nutrition 0.000 description 1
- 235000012660 Fragaria virginiana Nutrition 0.000 description 1
- 101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- CLYVKIFURLIDIL-UHFFFAOYSA-N ethyl 2-(5,5-dimethylcyclohexen-1-yl)acetate Chemical compound CC1(CCC=C(C1)CC(=O)OCC)C CLYVKIFURLIDIL-UHFFFAOYSA-N 0.000 description 1
- MLDNMOMQWZZDSU-UHFFFAOYSA-N ethyl 2-(cyclohexen-1-yl)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)C1=CCCCC1 MLDNMOMQWZZDSU-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000000704 physical effect Effects 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
- 238000010992 reflux Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania nowego 2-/5,5-dimetylo-2-cykloheksen-l- ylo/etanolu o wzorze 1.Zwiazek ten znajduje zastosowanie jako produkt posredni w syntezie substancji zapachowych.Istota wynalazku polega na tym, ze 5,5-dimetylo-2-cykloheksen-l-ylooctan etylu redukuje sie do 2-/5,5-dimetylo-2-cykloheksen- 1-ylo/etanolu, korzystnie wodorkiem litowoglinowym.Tak otrzymany 2-/5,5-dimetylo-2-cykloheksen-l-ylo/etanol poddany reakcji ekstryfikacji chlorkiem acetylu w obecnosci bezwodnej pirydyny prowadzi do powstania octanu 2-/5,5- dimetylo-2-cykloheksen-l-ylo/etylu o wzorze 2, który charakteryzuje sie srednio przyjemnym zapachem owocowo-kwiatowym z wybitna nuta poziomkowa. Ze wzgledu na ten walor nadaje sie on do stosowania w przemysle perfumeryjnym i spozywczym.Sposób wedlug wynalazku jest przedstawiony w przykladzie wykonania.Przyklad. W kolbie dwuszyjnej zaopatrzonej w chlodnice zwrotna zabezpieczona rurka z bezwodnym CaCh, wkraplacz i mieszadlo magnetyczne umieszcza sie 3,8 g/0,1 mola/Li AIH4 w 100 ml bezwodnego eteru etylowego. Do tak przygotowanej zawiesiny wkrapla sie przy intensyw¬ nym mieszaniu 39,2 g (0,2 mola) 5,5-dimetylo-2-cykloheksen-l-ylooctanu etylu. Przebieg reakcji kontroluje sie metoda chromatografii cienkowarstwowej. Mieszanine poreakcyjna hydrolizuje sie woda. Utworzony produkt ekstrahuje sie z warstwy wodnej po wysoleniu eterem etylowym.Ekstrakt przemywa sie nasyconym roztworem NaCl, suszy sie bezwodnym MgS04, a nastepnie usuwa sie rozpuszczalnik. Po destylacji pod zmniejszonym cisnieniem otrzymuje sie 29,0g, co stanowi 94% wydajnosci teoretycznej, 2-/5,5-dimetylo-2-cykloheksen- 1-ylo/etanolu o nastepuja¬ cych wlasnosciach fizycznych i spektralnych; temperatura wrzenia 90°C/798P.a.n20D= 1,4674 !H NMR/CC1, 5/1,17, l,22/2s, 6H, (CH-3/2C -CH = CH-/IR(cnr73350s), 1650/m/, 1370/s/, 1050/s/, 690/s/.Zastrzezenie patentowe Sposób wytwarzania mowego 2-/5,5-dimetylo-2-cykloheksen- 1-ylo/etanolu o wzorze 1, mienny tym, ze 5,5-dimetylo-2-cyklohcksen-l-ylooctan etylu redukuje sie do alkoholu, korzystniej wodorkiem Jitowoglinowym.137382 W^ór 1 Wzór! Pracownia Poligraficzna UP PRL. Naklad 100 egz.Cena 130 zl PLThe subject of the invention is a process for the preparation of a new 2- (5,5-dimethyl-2-cyclohexen-1-yl) ethanol of the formula 1. This compound is used as an intermediate in the synthesis of fragrances. The essence of the invention consists in the fact that 5.5 Ethyl-dimethyl-2-cyclohexen-1-ylacetate is reduced to 2- (5,5-dimethyl-2-cyclohexen-1-yl) ethanol, preferably lithium aluminum hydride. The 2- / 5,5-dimethyl-2-2 thus obtained cyclohexen-1-yl / ethanol, subjected to acetyl chloride extrusion in the presence of anhydrous pyridine, gives 2- (5,5-dimethyl-2-cyclohexen-1-yl / ethyl acetate) of the formula 2, which is characterized by a moderately pleasant fruity smell. floral with an outstanding note of wild strawberry. Due to this value, it is suitable for use in the perfumery and food industry. The method according to the invention is shown in the embodiment example. In a two-necked flask equipped with a reflux condenser, a secured tube with anhydrous CaCl2, an addition funnel and a magnetic stirrer are placed 3.8 g (0.1 mol / Li AlH4) in 100 ml of anhydrous diethyl ether. 39.2 g (0.2 mol) of ethyl 5,5-dimethyl-2-cyclohexen-1-ylacetate are added dropwise to the thus prepared suspension. The course of the reaction is monitored by thin layer chromatography. The reaction mixture is hydrolyzed with water. The product formed is extracted from the aqueous layer after salting out with diethyl ether. The extract is washed with saturated NaCl solution, dried with anhydrous MgSO 4, and then the solvent is removed. After distillation under reduced pressure, 29.0 g (94% of theory) of 2- (5,5-dimethyl-2-cyclohexen-1-yl) ethanol with the following physical and spectral properties are obtained; boiling point 90 ° C / 798P.a.n20D = 1.4674! H NMR / CC1.5 / 1.17.1.22 / 2s, 6H, (CH-3 / 2C -CH = CH- / IR (cnr73350s ), 1650 / m /, 1370 / s /, 1050 / s /, 690 / s /. Patent claim Process for the preparation of mical 2- (5,5-dimethyl-2-cyclohexen-1-yl) ethanol of formula 1, interchangeable with the fact that ethyl 5,5-dimethyl-2-cyclohcksen-1-ylacetate is reduced to alcohol, more preferably Jitovaluminum hydride. 137382 W ^ ór 1 Pattern! Printing workshop of the Polish People's Republic of Poland. Circulation 100 copies Price PLN 130 PL
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL24563384A PL137382B2 (en) | 1984-01-05 | 1984-01-05 | Process for preparing novel 2-/5,5-dimethyl-2-cyclohexen-1-yl/ethanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL24563384A PL137382B2 (en) | 1984-01-05 | 1984-01-05 | Process for preparing novel 2-/5,5-dimethyl-2-cyclohexen-1-yl/ethanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL245633A2 PL245633A2 (en) | 1984-11-08 |
| PL137382B2 true PL137382B2 (en) | 1986-05-31 |
Family
ID=20020082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL24563384A PL137382B2 (en) | 1984-01-05 | 1984-01-05 | Process for preparing novel 2-/5,5-dimethyl-2-cyclohexen-1-yl/ethanol |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL137382B2 (en) |
-
1984
- 1984-01-05 PL PL24563384A patent/PL137382B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL245633A2 (en) | 1984-11-08 |
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