DE1300571B - Verfahren zur Herstellung von 7, 8-Dimethoxy-2, 5-dimethyl-6-oxy-2-(4', 8', 12'-trimethyltridecyl)-chroman - Google Patents
Verfahren zur Herstellung von 7, 8-Dimethoxy-2, 5-dimethyl-6-oxy-2-(4', 8', 12'-trimethyltridecyl)-chromanInfo
- Publication number
- DE1300571B DE1300571B DEM63325A DEM0063325A DE1300571B DE 1300571 B DE1300571 B DE 1300571B DE M63325 A DEM63325 A DE M63325A DE M0063325 A DEM0063325 A DE M0063325A DE 1300571 B DE1300571 B DE 1300571B
- Authority
- DE
- Germany
- Prior art keywords
- dimethoxy
- oxy
- dimethyl
- trimethyltridecyl
- methyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- UIXPTCZPFCVOQF-UHFFFAOYSA-N ubiquinone-0 Chemical compound COC1=C(OC)C(=O)C(C)=CC1=O UIXPTCZPFCVOQF-UHFFFAOYSA-N 0.000 claims description 13
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 claims description 7
- BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 claims description 7
- HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 claims description 7
- BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 claims description 7
- BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 claims description 7
- KEVYVLWNCKMXJX-ZCNNSNEGSA-N Isophytol Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)C=C KEVYVLWNCKMXJX-ZCNNSNEGSA-N 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- DSBZYDDWLLIJJS-UHFFFAOYSA-N ubiquinol-0 Chemical compound COC1=C(O)C=C(C)C(O)=C1OC DSBZYDDWLLIJJS-UHFFFAOYSA-N 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GXCHUODWFNBVGV-UHFFFAOYSA-N 2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromene Chemical compound CC(CCCC1OC2=CC=CC=C2CC1)CCCC(CCCC(C)C)C GXCHUODWFNBVGV-UHFFFAOYSA-N 0.000 description 1
- SEBPXHSZHLFWRL-UHFFFAOYSA-N 3,4-dihydro-2,2,5,7,8-pentamethyl-2h-1-benzopyran-6-ol Chemical compound O1C(C)(C)CCC2=C1C(C)=C(C)C(O)=C2C SEBPXHSZHLFWRL-UHFFFAOYSA-N 0.000 description 1
- 206010002064 Anaemia macrocytic Diseases 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 201000006437 macrocytic anemia Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- -1 quinone compound Chemical class 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33228763A | 1963-12-20 | 1963-12-20 | |
| US605211A US3364234A (en) | 1963-12-20 | 1966-12-28 | Chroman compounds and preparation of same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1300571B true DE1300571B (de) | 1969-08-07 |
Family
ID=26988148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM63325A Pending DE1300571B (de) | 1963-12-20 | 1964-12-02 | Verfahren zur Herstellung von 7, 8-Dimethoxy-2, 5-dimethyl-6-oxy-2-(4', 8', 12'-trimethyltridecyl)-chroman |
Country Status (7)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH475977A (de) * | 1965-10-12 | 1969-07-31 | Hoffmann La Roche | Verfahren zur Herstellung eines Chromanderivates |
| US3459773A (en) * | 1966-12-27 | 1969-08-05 | Takasago Perfumery Co Ltd | Process for producing alpha-tocopherol and its esters |
| CH547278A (de) * | 1971-01-11 | 1974-03-29 | Hoffmann La Roche | Verfahren zur herstellung von chromanderivaten. |
| US3903317A (en) * | 1974-04-29 | 1975-09-02 | Hoffmann La Roche | Preservation of foodstuffs with synergistic antioxidant composition comprising ascorbic acid and 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid |
| US3986980A (en) * | 1974-04-29 | 1976-10-19 | Hoffmann-La Roche Inc. | Synergistic antioxidant composition comprising ascorbic acid and 6-hydroxy-2,5,7,8-tetramethylchroman-2- carboxylic acid |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB870638A (en) * | 1958-11-07 | 1961-06-14 | Hoffmann La Roche | Derivatives of 2,3-dimethoxy-5-methyl benzohydroquinone-(1,4) and a process for the manufacture thereof |
| US3026330A (en) * | 1960-05-09 | 1962-03-20 | Merck & Co Inc | Chroman compounds having antioxidant activity |
| GB927531A (en) * | 1958-08-27 | 1963-05-29 | Merck & Co Inc | Substituted benzoquinones and hydroquinones and their preparation |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA577760A (en) * | 1959-06-16 | Pittsburgh Plate Glass Company | Preparation of phenolic alcohols | |
| CA453166A (en) * | 1948-12-07 | Isler Otto | Dl-tocopherols and process for the manufacture of same | |
| DE731972C (de) * | 1938-04-01 | 1943-02-25 | Hoffmann La Roche | Verfahren zur Darstellung von d 1-Tocopherolen |
| GB529082A (en) * | 1938-05-31 | 1940-11-13 | Univ Minnesota | Improvements in chromanes and method of producing the same |
| DE713749C (de) * | 1938-07-20 | 1941-11-15 | Hoffmann La Roche & Co Akt Ges | Verfahren zur Darstellung von Kondensationsprodukten |
| DE711332C (de) * | 1938-12-07 | 1941-09-30 | Merck Chem Fab E | Verfahren zur Herstellung von Chromanen |
| AT215995B (de) * | 1958-11-07 | 1961-07-10 | Hoffmann La Roche | Verfahren zur Herstellung von neuen Chromanderivaten |
| AT246437B (de) * | 1961-05-29 | 1966-04-25 | Axel Richard Dr Techn Wejnarth | Gesinterte Legierung |
-
1964
- 1964-12-02 DE DEM63325A patent/DE1300571B/de active Pending
- 1964-12-09 GB GB50122/64A patent/GB1086183A/en not_active Expired
- 1964-12-16 BR BR165394/64A patent/BR6465394D0/pt unknown
- 1964-12-16 NL NL6414659A patent/NL6414659A/xx unknown
- 1964-12-17 FR FR1583155D patent/FR1583155A/fr not_active Expired
- 1964-12-18 CH CH1634564A patent/CH439323A/de unknown
-
1966
- 1966-12-28 US US605211A patent/US3364234A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB927531A (en) * | 1958-08-27 | 1963-05-29 | Merck & Co Inc | Substituted benzoquinones and hydroquinones and their preparation |
| GB870638A (en) * | 1958-11-07 | 1961-06-14 | Hoffmann La Roche | Derivatives of 2,3-dimethoxy-5-methyl benzohydroquinone-(1,4) and a process for the manufacture thereof |
| US3026330A (en) * | 1960-05-09 | 1962-03-20 | Merck & Co Inc | Chroman compounds having antioxidant activity |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1583155A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-10-24 |
| CH439323A (de) | 1967-07-15 |
| NL6414659A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-06-21 |
| BR6465394D0 (pt) | 1973-09-11 |
| GB1086183A (en) | 1967-10-04 |
| US3364234A (en) | 1968-01-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2945125C2 (de) | 4-(1,1-Dimethyläthyl)-4'-methoxydibenzoylmethan, Verfahren zu dessen Herstellung und dieses enthaltende Lichtschutzmittel | |
| DE2760005C2 (de) | Optisch aktive Norpinene und Verfahren zu ihrer Herstellung | |
| DE2042610B2 (de) | Verfahren zur Herstellung von Methylenmalonester | |
| DE1300571B (de) | Verfahren zur Herstellung von 7, 8-Dimethoxy-2, 5-dimethyl-6-oxy-2-(4', 8', 12'-trimethyltridecyl)-chroman | |
| DE4208477A1 (de) | Verfahren zur herstellung von vitamin e | |
| CH642536A5 (en) | Sunscreen agents | |
| DE2423485C2 (de) | 3-Oxotricyclo[2,2,1,0↑2↑↑,↑↑6↑]heptan-5-anti-carbonsäure und Verfahren zu ihrer Herstellung | |
| DE3009508A1 (de) | Verfahren zur herstellung von alpha -niederalkylfurocumarinen und neuartigen zwischenprodukten | |
| DE3153651C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2642670C2 (de) | Verfahren zur Herstellung von in 6-Stellung substituierten 2,3-Dimethoxy-5-methyl-1,4-benzochinonen | |
| DE2505237C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE1668957B1 (de) | Verfahren zur Herstellung von Maltol | |
| EP0087576A1 (de) | Verfahren zur Herstellung von Tocopherylacetat oder Tocopherylpropionat | |
| DE2834312C2 (de) | Verfahren zur Herstellung von 2[N-(2-Hydroxyäthyl)-N-niederalkylaminomethyl]-benzhydrolen | |
| EP0857722B1 (de) | Verfahren zur Herstellung von Tocopherylcarbonsäureestern oder Tocotrienylestern durch säurekatalysierte Umsetzung mit Carbonsäuren | |
| DE2232797C3 (de) | Halogenierte Dibenzylphenole mit antibakterieller Wirksamkeit, Verfahren zu deren Herstellung und antimikrobielle Mittel | |
| CH634811A5 (en) | Process for the oxidation of alkaryl compounds | |
| DE1793175C3 (de) | Verfahren zur Herstellung von 5-Benzyl-3-furancarbonsäure | |
| AT215995B (de) | Verfahren zur Herstellung von neuen Chromanderivaten | |
| DE2744956A1 (de) | Verfahren zur herstellung von n hoch 1 -(2'-furanidyl)-5-fluor- uracil | |
| DE757928C (de) | Verfahren zur Herstellung von Chromanverbindungen | |
| DE1493890C3 (de) | Verfahren zur Herstellung von ß- (5-Nitro-2-furyl)acrolein | |
| EP0492347B1 (de) | Verfahren zur Herstellung von threo-4-Alkoxy-5-(arylhydroxymethyl)-2(5H)-furanonen | |
| EP0005472B1 (de) | Verfahren zur Herstellung substituierter gamma-Halogencarbonsäureester | |
| EP0417543A2 (de) | Verfahren zur Herstellung von 3-Methylchinolin-8-carbonsäure |