CH394241A - Verfahren zur Herstellung von D-Tocopherol - Google Patents

Verfahren zur Herstellung von D-Tocopherol

Info

Publication number: CH394241A
Authority: CH; Switzerland
Prior art keywords: hydroxy; methyl; water; ether; acid
Prior art date: 1960-04-29

Application number

CH496260A

Other languages

German (de)

English (en)

Inventor

Albert Dr Langemann

Rudolf Dr Rueegg

Peter Dr Schudel

Ulrich Dr Schwieter

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1960-04-29

Filing date

1960-04-29

Publication date

1965-06-30

1960-04-29 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1960-04-29 Priority to CH496260A priority Critical patent/CH394241A/de

1961-04-20 Priority to BE602800A priority patent/BE602800A/fr

1961-04-25 Priority to GB1489161A priority patent/GB900217A/en

1961-04-28 Priority to ES0266987A priority patent/ES266987A1/es

1965-06-30 Publication of CH394241A publication Critical patent/CH394241A/de

Links

238000000034 method Methods 0.000 title claims description 9
239000011732 tocopherol Substances 0.000 title claims description 6
229960001295 tocopherol Drugs 0.000 title claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 44
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 12
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 10
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
229960000583 acetic acid Drugs 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
239000012362 glacial acetic acid Substances 0.000 claims description 7
239000000203 mixture Substances 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 6
230000002378 acidificating effect Effects 0.000 claims description 6
239000011592 zinc chloride Substances 0.000 claims description 6
235000005074 zinc chloride Nutrition 0.000 claims description 6
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 4
LXBHHIZIQVZGFN-UHFFFAOYSA-N 4-hydroxy-3-methylacetophenone Chemical compound CC(=O)C1=CC=C(O)C(C)=C1 LXBHHIZIQVZGFN-UHFFFAOYSA-N 0.000 claims description 4
229910015900 BF3 Inorganic materials 0.000 claims description 4
150000004967 organic peroxy acids Chemical class 0.000 claims description 4
UDGHTNPEJPFNIP-UHFFFAOYSA-N (4-hydroxy-3-methylphenyl)-phenylmethanone Chemical compound C1=C(O)C(C)=CC(C(=O)C=2C=CC=CC=2)=C1 UDGHTNPEJPFNIP-UHFFFAOYSA-N 0.000 claims description 3
239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 claims description 3
BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 claims description 3
HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 claims description 3
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 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
150000004965 peroxy acids Chemical class 0.000 claims description 3
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 3
238000002360 preparation method Methods 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
RZAOLEUBOLSFIP-UHFFFAOYSA-N (4-hydroxy-3-methylphenyl)-(4-nitrophenyl)methanone Chemical compound C1=C(O)C(C)=CC(C(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 RZAOLEUBOLSFIP-UHFFFAOYSA-N 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
XJSIOIUWJIMDDN-UHFFFAOYSA-N (4-hydroxy-3-methylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(O)C(C)=C1 XJSIOIUWJIMDDN-UHFFFAOYSA-N 0.000 description 2
ANPXVLAWWBTLAS-UHFFFAOYSA-N (4-hydroxy-3-methylphenyl) benzoate Chemical compound C1=C(O)C(C)=CC(OC(=O)C=2C=CC=CC=2)=C1 ANPXVLAWWBTLAS-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000002253 acid Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
-1 lithium aluminum hydride Chemical compound 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
235000010262 sodium metabisulphite Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
239000011627 DL-alpha-tocopherol Substances 0.000 description 1
235000001815 DL-alpha-tocopherol Nutrition 0.000 description 1
238000005618 Fries rearrangement reaction Methods 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
238000000199 molecular distillation Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
235000010384 tocopherol Nutrition 0.000 description 1
238000005406 washing Methods 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH496260A 1960-04-29 1960-04-29 Verfahren zur Herstellung von D-Tocopherol CH394241A (de)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CH496260A CH394241A (de)	1960-04-29	1960-04-29	Verfahren zur Herstellung von D-Tocopherol
BE602800A BE602800A (fr)	1960-04-29	1961-04-20	Procédé pour la préparation de alpha-tocophérol
GB1489161A GB900217A (en)	1960-04-29	1961-04-25	A process for the manufacture of ú-úsú8ú(úßtocopherol
ES0266987A ES266987A1 (es)	1960-04-29	1961-04-28	Un procedimiento para la preparaciën de delta-tocoferol

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH496260A CH394241A (de)	1960-04-29	1960-04-29	Verfahren zur Herstellung von D-Tocopherol

Publications (1)

Publication Number	Publication Date
CH394241A true CH394241A (de)	1965-06-30

Family

ID=4285549

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH496260A CH394241A (de)	1960-04-29	1960-04-29	Verfahren zur Herstellung von D-Tocopherol

Country Status (4)

Country	Link
BE (1)	BE602800A (fr)
CH (1)	CH394241A (fr)
ES (1)	ES266987A1 (fr)
GB (1)	GB900217A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5081155A (en) *	1989-04-13	1992-01-14	Henkel Corporation	Hydroxy aromatic ketones

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN114306291B (zh) *	2022-01-13	2023-06-27	云南大学	一种化合物在预防和/或治疗癌症中的用途

1960
- 1960-04-29 CH CH496260A patent/CH394241A/de unknown
1961
- 1961-04-20 BE BE602800A patent/BE602800A/fr unknown
- 1961-04-25 GB GB1489161A patent/GB900217A/en not_active Expired
- 1961-04-28 ES ES0266987A patent/ES266987A1/es not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5081155A (en) *	1989-04-13	1992-01-14	Henkel Corporation	Hydroxy aromatic ketones

Also Published As

Publication number	Publication date
BE602800A (fr)	1961-10-20
ES266987A1 (es)	1961-11-01
GB900217A (en)	1962-07-04

Publication	Publication Date	Title
DE2202689A1 (de)	1972-08-03	Neue Zwischenprodukte der Vitamin-A-Synthese
CH394241A (de)	1965-06-30	Verfahren zur Herstellung von D-Tocopherol
CH311607A (de)	1955-11-30	Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6-methyl-anilids).
US2533086A (en)	1950-12-05	Hydroxymethylthianaphthene
DE2609015A1 (de)	1976-09-16	Verfahren zur herstellung von benz (f)-2,5-oxazocinen
DE574838C (de)	1933-04-22	Verfahren zur Darstellung von cyclischen Glykolen und ihren Derivaten bzw. von Ketonen
AT203485B (de)	1959-05-25	Verfahren zur Herstellung von neuen Dinitrophenylmethacrylaten
DE1184757C2 (de)	1981-06-04	Verfahren zur herstellung von reaktionsprodukten aus 3,4-dimethylphenol
DE951811C (de)	1956-11-08	Verfahren zur Herstellung von Propiolsaeure
DE860637C (de)	1952-12-22	Verfahren zur Herstellung schwefelhaltiger cyclischer organischer Verbindungen
DE826133C (de)	1951-12-27	Verfahren zur Herstellung von Dihydroresorcin-carbaminsaeureestern
DE1470264C3 (de)	1975-12-04	Verfahren zur Herstellung von 1-Phenyl-1 - eckige Klammer auf thienyl-(2) eckige Klammer zu -carbinolen
AT215993B (de)	1961-07-10	Verfahren zur Herstellung von neuen 4-Oxo-2-(halogenalkyl)-2,3-dihydro-[benzo-1,3-oxazinen]
AT228182B (de)	1963-07-10	Verfahren zur Herstellung von Triolen
DE2365421C3 (de)	1980-11-13	Verfahren zur Herstellung von Methylfumardialdehydmonoacetalen
DE871449C (de)	1953-03-23	Verfahren zur Herstellung des Pentaerythrit-dichlorhydrin-monoschwefligsaeureesters
AT226692B (de)	1963-04-10	Verfahren zur Herstellung von neuen α-Pyrrolidino-valerophenonen
DE1217372B (de)	1966-05-26	Verfahren zur Herstellung von Cycloalkan- und Cycloalkencarbonsäuren bzw. deren Estern
DE935433C (de)	1955-11-17	Verfahren zur Herstellung von Glycidestern von Sulfonsaeuren
DE871751C (de)	1953-03-26	Verfahren zur Gewinnung des Pentaerythrit-dichlorhydrinmonoschwefligsaeureesters
CH206596A (de)	1939-08-15	Verfahren zur Herstellung eines Gemisches kernalkylierter aromatischer Verbindungen.
DE947308C (de)	1956-08-16	Verfahren zur Herstellung von Hydrochinon
CH287861A (de)	1952-12-31	Verfahren zur Herstellung einer Verbindung der Androstenreihe.
DE1298523B (de)	1969-07-03	Verfahren zur Herstellung substituierter Dibenzo-[a,d] Cycloheptanverbindungen
CH207606A (de)	1939-11-15	Verfahren zur Herstellung eines Kondensationsproduktes aus B-Tocopherol und Allylhalogenid.

CH394241A - Verfahren zur Herstellung von D-Tocopherol - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (4)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4285549

Family Applications (1)

Country Status (4)

Cited By (1)

Families Citing this family (1)

Cited By (1)

Also Published As

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