PL423671A1 - Ethyl (2E)-2-[(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexylidene]butanoate and method for producing it - Google Patents
Ethyl (2E)-2-[(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexylidene]butanoate and method for producing itInfo
- Publication number
- PL423671A1 PL423671A1 PL423671A PL42367117A PL423671A1 PL 423671 A1 PL423671 A1 PL 423671A1 PL 423671 A PL423671 A PL 423671A PL 42367117 A PL42367117 A PL 42367117A PL 423671 A1 PL423671 A1 PL 423671A1
- Authority
- PL
- Poland
- Prior art keywords
- butanoate
- ethyl
- cyclohexylidene
- prop
- methyl
- Prior art date
Links
- WULJHPLHRZZNGH-QWBYSSASSA-N ethyl (2E)-2-[(2R,5R)-2-methyl-5-prop-1-en-2-ylcyclohexylidene]butanoate Chemical compound C[C@H]1\C(\C[C@@H](CC1)C(=C)C)=C(\C(=O)OCC)/CC WULJHPLHRZZNGH-QWBYSSASSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 238000004440 column chromatography Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000002537 cosmetic Substances 0.000 abstract 1
- GYUCVQSNZFRDRL-UHFFFAOYSA-N ethyl 2-diethoxyphosphorylbutanoate Chemical compound CCOC(=O)C(CC)P(=O)(OCC)OCC GYUCVQSNZFRDRL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000796 flavoring agent Substances 0.000 abstract 1
- 235000019634 flavors Nutrition 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 238000004809 thin layer chromatography Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Seasonings (AREA)
Abstract
Zgłoszenie dotyczy (2E)-2-[(2R,5R)-2-metylo-5-(prop-1-en-2-ylo)cykloheksylideno]butanianem etylu o wzorze 1, który znajduje zastosowanie w przemyśle kosmetycznym i spożywczym jako związek zapachowy. Przedmiotem zgłoszenia jest też sposób wytwarzania (2E)-2-[(2R,5R)-2-metylo-5-(prop-1-en-2-ylo)cykloheksylideno]butanianu etylu o wzorze 1 znamienny tym, że (+)-dihydrokarown poddaje się reakcji HWE z użyciem 2-(dietoksyfosforyl)butanianu etylu jako reagenta i tetrahydrofuranu jako środowiska reakcji, przy czym reakcja prowadzona jest w łaźni lodowej, a po zakończeniu procesu odparowuje się rozpuszczalniki, a produkt oczyszcza się przy wykorzystaniu chromatografii kolumnowej, natomiast przebieg reakcji kontroluje się przy wykorzystaniu chromatografii cienkowarstwowej.The application concerns ethyl (2E) -2 - [(2R, 5R) -2-methyl-5- (prop-1-en-2-yl) cyclohexylidene] butanoate of formula 1 which is used in the cosmetics and food industry as a compound flavor. The subject of the application is also a process for producing ethyl (2E) -2 - [(2R, 5R) -2-methyl-5- (prop-1-en-2-yl) cyclohexylidene] butanoate of formula 1, characterized in that (+) -dihydrocarbyl is reacted with HWE using ethyl 2- (diethoxyphosphoryl) butanoate as a reactant and tetrahydrofuran as a reaction medium, the reaction is carried out in an ice bath and after the process the solvents are evaporated off and the product is purified using column chromatography, while the course of the reaction is monitored using thin layer chromatography.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL423671A PL234190B1 (en) | 2017-12-01 | 2017-12-01 | Ethyl (2E)-2-[(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexylidene]butanoate and method for producing it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL423671A PL234190B1 (en) | 2017-12-01 | 2017-12-01 | Ethyl (2E)-2-[(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexylidene]butanoate and method for producing it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL423671A1 true PL423671A1 (en) | 2019-06-03 |
| PL234190B1 PL234190B1 (en) | 2020-01-31 |
Family
ID=66649292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL423671A PL234190B1 (en) | 2017-12-01 | 2017-12-01 | Ethyl (2E)-2-[(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexylidene]butanoate and method for producing it |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL234190B1 (en) |
-
2017
- 2017-12-01 PL PL423671A patent/PL234190B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL234190B1 (en) | 2020-01-31 |
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