DE2209372C2 - 3 Oxa bicyclo eckige Klammer auf 10 3 0 eckige Klammer zu pentadecen (6) und ein Verfahren zu dessen Her stellung sowie dessen Verwendung als Riechstoff - Google Patents
3 Oxa bicyclo eckige Klammer auf 10 3 0 eckige Klammer zu pentadecen (6) und ein Verfahren zu dessen Her stellung sowie dessen Verwendung als RiechstoffInfo
- Publication number
- DE2209372C2 DE2209372C2 DE2209372A DE2209372A DE2209372C2 DE 2209372 C2 DE2209372 C2 DE 2209372C2 DE 2209372 A DE2209372 A DE 2209372A DE 2209372 A DE2209372 A DE 2209372A DE 2209372 C2 DE2209372 C2 DE 2209372C2
- Authority
- DE
- Germany
- Prior art keywords
- oxa
- fragrance
- acid
- pentadecen
- bicyclo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000003205 fragrance Substances 0.000 title claims description 9
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 title claims 6
- 238000000034 method Methods 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000000203 mixture Substances 0.000 claims description 6
- 239000002304 perfume Substances 0.000 claims description 4
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical class O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 8
- 239000003054 catalyst Substances 0.000 claims 6
- 239000002841 Lewis acid Substances 0.000 claims 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims 4
- 229960000583 acetic acid Drugs 0.000 claims 4
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 claims 4
- 239000012362 glacial acetic acid Substances 0.000 claims 4
- 150000007517 lewis acids Chemical class 0.000 claims 4
- 229920002866 paraformaldehyde Polymers 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 238000010478 Prins reaction Methods 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims 1
- ZOKYTRIEIDWYSG-PKNBQFBNSA-N (e)-dodec-5-ene Chemical compound CCCCCC\C=C\CCCC ZOKYTRIEIDWYSG-PKNBQFBNSA-N 0.000 claims 1
- 150000000093 1,3-dioxanes Chemical class 0.000 claims 1
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 claims 1
- YCIXWYOBMVNGTB-UHFFFAOYSA-N 3-methyl-2-pentylcyclopent-2-en-1-one Chemical compound CCCCCC1=C(C)CCC1=O YCIXWYOBMVNGTB-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 240000007436 Cananga odorata Species 0.000 claims 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims 1
- 241000402754 Erythranthe moschata Species 0.000 claims 1
- 239000005770 Eugenol Substances 0.000 claims 1
- 239000005792 Geraniol Substances 0.000 claims 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000001464 adherent effect Effects 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- 229940007550 benzyl acetate Drugs 0.000 claims 1
- 229960002903 benzyl benzoate Drugs 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- UCIYGNATMHQYCT-OWOJBTEDSA-N cyclodecene Chemical compound C1CCCC\C=C\CCC1 UCIYGNATMHQYCT-OWOJBTEDSA-N 0.000 claims 1
- 229960002217 eugenol Drugs 0.000 claims 1
- 239000000834 fixative Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 229940113087 geraniol Drugs 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000001819 mass spectrum Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 1
- 229940067107 phenylethyl alcohol Drugs 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- 239000001724 (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulen-6-yl) acetate Substances 0.000 description 1
- VMUXSMXIQBNMGZ-UHFFFAOYSA-N 3,4-dihydrocoumarin Chemical compound C1=CC=C2OC(=O)CCC2=C1 VMUXSMXIQBNMGZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- 240000002505 Pogostemon cablin Species 0.000 description 1
- 235000011751 Pogostemon cablin Nutrition 0.000 description 1
- 240000000513 Santalum album Species 0.000 description 1
- 235000008632 Santalum album Nutrition 0.000 description 1
- UAVFEMBKDRODDE-UHFFFAOYSA-N Vetiveryl acetate Chemical compound CC1CC(OC(C)=O)C=C(C)C2CC(=C(C)C)CC12 UAVFEMBKDRODDE-UHFFFAOYSA-N 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- DMSHWWDRAYHEBS-UHFFFAOYSA-N dihydrocoumarin Natural products C1CC(=O)OC2=C1C=C(OC)C(OC)=C2 DMSHWWDRAYHEBS-UHFFFAOYSA-N 0.000 description 1
- 229940073505 ethyl vanillin Drugs 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2209372A DE2209372C2 (de) | 1972-02-28 | 1972-02-28 | 3 Oxa bicyclo eckige Klammer auf 10 3 0 eckige Klammer zu pentadecen (6) und ein Verfahren zu dessen Her stellung sowie dessen Verwendung als Riechstoff |
| NL7203202A NL7203202A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-02-28 | 1972-03-10 | |
| CH354572A CH567496A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-02-28 | 1972-03-10 | |
| FR7210397A FR2176588B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-02-28 | 1972-03-24 | |
| JP47040965A JPS5121052B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-02-28 | 1972-04-25 | |
| US00268091A US3824258A (en) | 1972-02-28 | 1972-06-30 | 3-oxabicyclo-(10.3.0)pentadecene-(6) and its preparation |
| GB5236472A GB1398608A (en) | 1972-02-28 | 1972-11-13 | Oxabicyclopentadecene |
| US429651A US3893953A (en) | 1972-02-28 | 1973-12-28 | 3-Oxabicyclo{8 10.3.0{9 pentadecene-(6), its preparation and its use as a perfuming agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2209372A DE2209372C2 (de) | 1972-02-28 | 1972-02-28 | 3 Oxa bicyclo eckige Klammer auf 10 3 0 eckige Klammer zu pentadecen (6) und ein Verfahren zu dessen Her stellung sowie dessen Verwendung als Riechstoff |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2209372B1 DE2209372B1 (de) | 1973-02-15 |
| DE2209372A1 DE2209372A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-02-15 |
| DE2209372C2 true DE2209372C2 (de) | 1973-09-27 |
Family
ID=5837342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2209372A Expired DE2209372C2 (de) | 1972-02-28 | 1972-02-28 | 3 Oxa bicyclo eckige Klammer auf 10 3 0 eckige Klammer zu pentadecen (6) und ein Verfahren zu dessen Her stellung sowie dessen Verwendung als Riechstoff |
Country Status (7)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3893953A (en) * | 1972-02-28 | 1975-07-08 | Dragoco Gerberding Co Gmbh | 3-Oxabicyclo{8 10.3.0{9 pentadecene-(6), its preparation and its use as a perfuming agent |
| DE2810107C2 (de) * | 1978-03-09 | 1987-01-22 | Henkel KGaA, 4000 Düsseldorf | 13-Oxabicyclo[10.3.0]pentadecan, Verfahren zu dessen Herstellung und dessen Verwendung als Riechstoff |
-
1972
- 1972-02-28 DE DE2209372A patent/DE2209372C2/de not_active Expired
- 1972-03-10 CH CH354572A patent/CH567496A5/xx not_active IP Right Cessation
- 1972-03-10 NL NL7203202A patent/NL7203202A/xx not_active Application Discontinuation
- 1972-03-24 FR FR7210397A patent/FR2176588B1/fr not_active Expired
- 1972-04-25 JP JP47040965A patent/JPS5121052B2/ja not_active Expired
- 1972-06-30 US US00268091A patent/US3824258A/en not_active Expired - Lifetime
- 1972-11-13 GB GB5236472A patent/GB1398608A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1398608A (en) | 1975-06-25 |
| DE2209372B1 (de) | 1973-02-15 |
| US3824258A (en) | 1974-07-16 |
| DE2209372A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-02-15 |
| JPS4892359A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-11-30 |
| NL7203202A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-08-30 |
| JPS5121052B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-06-30 |
| FR2176588B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-12-13 |
| CH567496A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-15 |
| FR2176588A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-11-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |