MD2019C2 - Process for obtaining of 8a-acetoxy-14,15-bisnorlabdan-13-one from sclareol diacetate - Google Patents
Process for obtaining of 8a-acetoxy-14,15-bisnorlabdan-13-one from sclareol diacetate Download PDFInfo
- Publication number
- MD2019C2 MD2019C2 MDA20010043A MD20010043A MD2019C2 MD 2019 C2 MD2019 C2 MD 2019C2 MD A20010043 A MDA20010043 A MD A20010043A MD 20010043 A MD20010043 A MD 20010043A MD 2019 C2 MD2019 C2 MD 2019C2
- Authority
- MD
- Moldova
- Prior art keywords
- diacetate
- sclareol
- bisnorlabdan
- acetoxy
- obtaining
- Prior art date
Links
- XVULBTBTFGYVRC-HHUCQEJWSA-N sclareol Chemical compound CC1(C)CCC[C@]2(C)[C@@H](CC[C@](O)(C)C=C)[C@](C)(O)CC[C@H]21 XVULBTBTFGYVRC-HHUCQEJWSA-N 0.000 title abstract 6
- XVULBTBTFGYVRC-UHFFFAOYSA-N Episclareol Natural products CC1(C)CCCC2(C)C(CCC(O)(C)C=C)C(C)(O)CCC21 XVULBTBTFGYVRC-UHFFFAOYSA-N 0.000 title abstract 3
- LAEIZWJAQRGPDA-UHFFFAOYSA-N Manoyloxid Natural products CC1(C)CCCC2(C)C3CC=C(C)OC3(C)CCC21 LAEIZWJAQRGPDA-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 238000006385 ozonation reaction Methods 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a process for obtaining the 8α-acetoxy-14,15-bisnorlabdan-13-one compound from sclareol diacetate, intermediate in the synthesis of compounds with strong amber smell, used in perfumery industry.The process consists in oxidation by ozonation of sclareol diacetate in a methanol and methylene chloride mixture solution at a temperature of -80...+24°C, treatment of the ozonation product with a mixture of equivalent amounts of ferrous sulphate heptahydrate and copper diacetate monohydrate at the room temperature, with the subsequent separation and purification of the final product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20010043A MD2019C2 (en) | 2001-02-22 | 2001-02-22 | Process for obtaining of 8a-acetoxy-14,15-bisnorlabdan-13-one from sclareol diacetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20010043A MD2019C2 (en) | 2001-02-22 | 2001-02-22 | Process for obtaining of 8a-acetoxy-14,15-bisnorlabdan-13-one from sclareol diacetate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| MD20010043A MD20010043A (en) | 2002-09-30 |
| MD2019B2 MD2019B2 (en) | 2002-10-31 |
| MD2019C2 true MD2019C2 (en) | 2003-04-30 |
Family
ID=19739757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20010043A MD2019C2 (en) | 2001-02-22 | 2001-02-22 | Process for obtaining of 8a-acetoxy-14,15-bisnorlabdan-13-one from sclareol diacetate |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD2019C2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD4248C1 (en) * | 2013-04-19 | 2014-03-31 | Институт Химии Академии Наук Молдовы | Process for producing 14,15-bisnorlabdane-8(9)-en-13-one |
-
2001
- 2001-02-22 MD MDA20010043A patent/MD2019C2/en not_active IP Right Cessation
Non-Patent Citations (8)
| Title |
|---|
| D.B. Bigley, N.A..J. Rogers, J.A. Barltrop, J. Chem. Soc., nr. 11, 4613, 1960 * |
| G. Ohloff, Helv. Chim. Acta, 1958, vol. 41, nr. 3, p. 845 * |
| I.C. Coste-Maniere, J.P. Zahra, B. Waegell, Tetrahedron Letters, 1988,29, nr. 9, p. 1017, * |
| J.G. Urones, J.S. Marcos, P. Basabe, A. Gomez, A. Estrela, A.M. Lithgow, Natural Product Letters, 1994, 5, nr. 2, p. 217 * |
| J.G. Urones, P. Basabe, J.S. Marcos, J.G. Gonzales, V. Jimenez, J. Sexmero, A.M. Lithgow, Tetrahedron, 1992, vol. 48, nr. 45, p. 1991 * |
| J.P. Zahra, F. Chauvet, J. Coste-Maniere, P. Martres, P. Perfetti, B. Waegell, Bull. Soc. France, 1997, vol. 130, nr. 10/11, p. 1001 * |
| Ph.A. Christensen, Tetrahedron, 1988, vol. 44, nr. 7, p. 192 * |
| Влад П.Ф., Колца М.Н. Синтез и применение душистых веществ из лабдановых дитерпеноидов. Кишинев, Штиинца, 1988, с. 7-15 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD2019B2 (en) | 2002-10-31 |
| MD20010043A (en) | 2002-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |