DE2225612C2 - Cyclische Methyl-fumardialdehyd-monoacetale und Verfahren zu ihrer Herstellung - Google Patents
Cyclische Methyl-fumardialdehyd-monoacetale und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2225612C2 DE2225612C2 DE19722225612 DE2225612A DE2225612C2 DE 2225612 C2 DE2225612 C2 DE 2225612C2 DE 19722225612 DE19722225612 DE 19722225612 DE 2225612 A DE2225612 A DE 2225612A DE 2225612 C2 DE2225612 C2 DE 2225612C2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- retinal
- acetal
- vitamin
- fumaric
- 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
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 title claims description 10
- 125000004122 cyclic group Chemical group 0.000 title claims description 10
- 238000000034 method Methods 0.000 title description 23
- 238000002360 preparation method Methods 0.000 title description 3
- 235000020945 retinal Nutrition 0.000 description 19
- 239000011604 retinal Substances 0.000 description 19
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 19
- 230000002207 retinal effect Effects 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 11
- -1 nickel peroxide Chemical class 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 150000001241 acetals Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 238000007239 Wittig reaction Methods 0.000 description 7
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 4
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000019155 vitamin A Nutrition 0.000 description 4
- 239000011719 vitamin A Substances 0.000 description 4
- 229940045997 vitamin a Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000021466 carotenoid Nutrition 0.000 description 3
- 150000001747 carotenoids Chemical class 0.000 description 3
- KPVWDKBJLIDKEP-UHFFFAOYSA-L dihydroxy(dioxo)chromium;sulfuric acid Chemical compound OS(O)(=O)=O.O[Cr](O)(=O)=O KPVWDKBJLIDKEP-UHFFFAOYSA-L 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960000342 retinol acetate Drugs 0.000 description 3
- 235000019173 retinyl acetate Nutrition 0.000 description 3
- 239000011770 retinyl acetate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NCYCYZXNIZJOKI-OVSJKPMPSA-N Retinaldehyde Chemical compound O=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-OVSJKPMPSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000007295 Wittig olefination reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 210000001525 retina Anatomy 0.000 description 2
- QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000002266 vitamin A derivatives Chemical class 0.000 description 2
- USBJWIKCHJDWPF-GORDUTHDSA-N (e)-2-methylbut-2-enedial Chemical compound O=CC(/C)=C/C=O USBJWIKCHJDWPF-GORDUTHDSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- QXQQCYKFELYFGP-ZZXKWVIFSA-N [(e)-2-methyl-4-oxobut-2-enyl] acetate Chemical compound CC(=O)OC\C(C)=C\C=O QXQQCYKFELYFGP-ZZXKWVIFSA-N 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- JZULKTSSLJNBQJ-UHFFFAOYSA-N chromium;sulfuric acid Chemical compound [Cr].OS(O)(=O)=O JZULKTSSLJNBQJ-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 150000004508 retinoic acid derivatives Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722225612 DE2225612C2 (de) | 1972-05-26 | 1972-05-26 | Cyclische Methyl-fumardialdehyd-monoacetale und Verfahren zu ihrer Herstellung |
| CH734273A CH585689A5 (enExample) | 1972-05-26 | 1973-05-23 | |
| CH734173A CH579068A5 (enExample) | 1972-05-26 | 1973-05-23 | |
| FR7318925A FR2189370B1 (enExample) | 1972-05-26 | 1973-05-24 | |
| FR7318924A FR2189359B1 (enExample) | 1972-05-26 | 1973-05-24 | |
| GB2510773A GB1422684A (en) | 1972-05-26 | 1973-05-25 | Methylfumaraldehyde monoacetals and process for making them |
| GB2510873A GB1421942A (en) | 1972-05-26 | 1973-05-25 | 2-3-methyl-1-acetoxy-4-alkoxy-phenoxy-1,3-butadiens and their manufacture and use |
| US05/363,861 US4009202A (en) | 1972-05-26 | 1973-05-25 | 2(or 3)-methyl-1-acetoxy-4-alkoxy (or phenoxy)-1,3-butadienes |
| JP5786273A JPS5523829B2 (enExample) | 1972-05-26 | 1973-05-25 | |
| JP5826573A JPS5617334B2 (enExample) | 1972-05-26 | 1973-05-26 | |
| US05/891,540 US4192806A (en) | 1972-05-26 | 1978-03-30 | Methyl fumaraldehyde monoacetals and process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722225612 DE2225612C2 (de) | 1972-05-26 | 1972-05-26 | Cyclische Methyl-fumardialdehyd-monoacetale und Verfahren zu ihrer Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2225612A1 DE2225612A1 (de) | 1973-12-20 |
| DE2225612C2 true DE2225612C2 (de) | 1982-07-01 |
Family
ID=5845937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722225612 Expired DE2225612C2 (de) | 1972-05-26 | 1972-05-26 | Cyclische Methyl-fumardialdehyd-monoacetale und Verfahren zu ihrer Herstellung |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5523829B2 (enExample) |
| CH (1) | CH579068A5 (enExample) |
| DE (1) | DE2225612C2 (enExample) |
| FR (1) | FR2189359B1 (enExample) |
| GB (1) | GB1422684A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4410719A (en) | 1981-07-01 | 1983-10-18 | Basf Aktiengesellschaft | Preparation of 2-alkyl-4,4-diacyloxybut-2-enals |
| EP0235532A1 (de) * | 1986-01-25 | 1987-09-09 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 4-Monoacetalen des 2-Methyl-2-buten-1,4-dials |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2842715A1 (de) * | 1978-09-30 | 1980-04-10 | Basf Ag | 3-chlor-3-methyl-butan- bzw. 3-methyl- 2-buten-1,4-dial-bis-acetale, ein verfahren zur herstellung dieser verbindungen sowie deren verwendung |
| DE2917413A1 (de) * | 1979-04-28 | 1980-11-06 | Basf Ag | Verfahren zur herstellung von cyclischen acetalen von trans-4-chlor-3-methyl- 2-buten-1-al sowie von trans-3-methyl-2- buten-1,4-dial-1-monoacetalen |
| DE3617409A1 (de) * | 1986-05-23 | 1987-11-26 | Basf Ag | Verfahren zur herstellung von 4-acetalen des butendial-(1,4) und neue acetale des butendial-(1,4) |
| DE4106907A1 (de) * | 1991-03-05 | 1992-09-10 | Basf Ag | Verfahren zur herstellung von 3-alkoxycarbonylpropenalen und 3-dialkoxymethylpropenalen |
-
1972
- 1972-05-26 DE DE19722225612 patent/DE2225612C2/de not_active Expired
-
1973
- 1973-05-23 CH CH734173A patent/CH579068A5/xx not_active IP Right Cessation
- 1973-05-24 FR FR7318924A patent/FR2189359B1/fr not_active Expired
- 1973-05-25 JP JP5786273A patent/JPS5523829B2/ja not_active Expired
- 1973-05-25 GB GB2510773A patent/GB1422684A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4410719A (en) | 1981-07-01 | 1983-10-18 | Basf Aktiengesellschaft | Preparation of 2-alkyl-4,4-diacyloxybut-2-enals |
| EP0235532A1 (de) * | 1986-01-25 | 1987-09-09 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 4-Monoacetalen des 2-Methyl-2-buten-1,4-dials |
Also Published As
| Publication number | Publication date |
|---|---|
| CH579068A5 (enExample) | 1976-08-31 |
| FR2189359B1 (enExample) | 1976-06-11 |
| GB1422684A (en) | 1976-01-28 |
| FR2189359A1 (enExample) | 1974-01-25 |
| JPS5523829B2 (enExample) | 1980-06-25 |
| JPS4954383A (enExample) | 1974-05-27 |
| DE2225612A1 (de) | 1973-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination |