CH376495A - Verfahren zur Herstellung von ungesättigten cyclischen Ketonen - Google Patents

Verfahren zur Herstellung von ungesättigten cyclischen Ketonen

Info

Publication number: CH376495A
Authority: CH; Switzerland
Prior art keywords: alcohol; sep; phosphoric acid; trimethyl; starting material
Prior art date: 1958-12-17

Application number

CH6741158A

Other languages

German (de)

English (en)

Inventor

Waldemar Dr Guex

Roman Dr Marbet

Marc Dr Montavon

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.)

1958-12-17

Filing date

1958-12-17

Publication date

1964-04-15

1958-12-17 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1958-12-17 Priority to CH6741158A priority Critical patent/CH376495A/de

1959-12-09 Priority to BE585463A priority patent/BE585463A/fr

1964-04-15 Publication of CH376495A publication Critical patent/CH376495A/de

Links

238000000034 method Methods 0.000 title claims description 12
150000003997 cyclic ketones Chemical class 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 9
230000002378 acidificating effect Effects 0.000 claims description 7
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 6
ZCLASKGHHKNPGK-UHFFFAOYSA-N CC(=CC(=CC(C)(OCC)OCC)OCC)CCCC(C)C Chemical compound CC(=CC(=CC(C)(OCC)OCC)OCC)CCCC(C)C ZCLASKGHHKNPGK-UHFFFAOYSA-N 0.000 claims description 5
230000008030 elimination Effects 0.000 claims description 5
238000003379 elimination reaction Methods 0.000 claims description 5
APFGORMRDLKILA-UHFFFAOYSA-N CC(=CC(=CC(C)(OCC)OCC)OCC)CCC(C(C)C)C Chemical compound CC(=CC(=CC(C)(OCC)OCC)OCC)CCC(C(C)C)C APFGORMRDLKILA-UHFFFAOYSA-N 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 4
238000004821 distillation Methods 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 4
IRVGWDJFZXOKDK-FNORWQNLSA-N (3e)-trideca-1,3-diene Chemical compound CCCCCCCCC\C=C\C=C IRVGWDJFZXOKDK-FNORWQNLSA-N 0.000 claims 1
OTRFASAQWXIUMU-UHFFFAOYSA-N CCCC(C)C(C)CCC(C)=CC(OCC)=C(C)C(C)(OCC)OCC Chemical compound CCCC(C)C(C)CCC(C)=CC(OCC)=C(C)C(C)(OCC)OCC OTRFASAQWXIUMU-UHFFFAOYSA-N 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
238000009835 boiling Methods 0.000 description 8
-1 6, 10-dimethyl-2,2,4-trimethoxy-dodecadiene Chemical compound 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
239000000203 mixture Substances 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
ALYUGEXDFUNPTI-UHFFFAOYSA-N CC(C(C)(OCC)OCC)=C(C=C(CCCC(C)C)C)OCC Chemical compound CC(C(C)(OCC)OCC)=C(C=C(CCCC(C)C)C)OCC ALYUGEXDFUNPTI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000001241 acetals Chemical class 0.000 description 4
239000005457 ice water Substances 0.000 description 4
ZLFHFJJIMSZNHV-UHFFFAOYSA-N 2-ethoxybut-1-ene Chemical compound CCOC(=C)CC ZLFHFJJIMSZNHV-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
235000005074 zinc chloride Nutrition 0.000 description 3
239000011592 zinc chloride Substances 0.000 description 3
FSGHEPDRMHVUCQ-UHFFFAOYSA-N 2-ethoxyprop-1-ene Chemical compound CCOC(C)=C FSGHEPDRMHVUCQ-UHFFFAOYSA-N 0.000 description 2
WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-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
229940043350 citral Drugs 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
239000000446 fuel Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
BCEQJZNLIKMDEU-UHFFFAOYSA-N (6E)-3,7-dimethylnona-2,6-dienal Chemical compound CCC(C)=CCCC(C)=CC=O BCEQJZNLIKMDEU-UHFFFAOYSA-N 0.000 description 1
JRJBVWJSTHECJK-PKNBQFBNSA-N 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one Chemical compound CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-PKNBQFBNSA-N 0.000 description 1
MEVCUFMTQSTGCR-UHFFFAOYSA-N CC(C(=C)OCC)=CC=C(C=CCC(C)C)C Chemical compound CC(C(=C)OCC)=CC=C(C=CCC(C)C)C MEVCUFMTQSTGCR-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000001941 cymbopogon citratus dc and cymbopogon flexuosus oil Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002084 enol ethers Chemical class 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
UZFLPKAIBPNNCA-FPLPWBNLSA-N α-ionone Chemical compound CC(=O)\C=C/C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-FPLPWBNLSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
- C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH6741158A 1958-12-17 1958-12-17 Verfahren zur Herstellung von ungesättigten cyclischen Ketonen CH376495A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH6741158A CH376495A (de)	1958-12-17	1958-12-17	Verfahren zur Herstellung von ungesättigten cyclischen Ketonen
BE585463A BE585463A (fr)	1958-12-17	1959-12-09	Procédé pour la préparation de cétones cycliques non-saturées.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH6741158A CH376495A (de)	1958-12-17	1958-12-17	Verfahren zur Herstellung von ungesättigten cyclischen Ketonen

Publications (1)

Publication Number	Publication Date
CH376495A true CH376495A (de)	1964-04-15

Family

ID=4527935

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6741158A CH376495A (de)	1958-12-17	1958-12-17	Verfahren zur Herstellung von ungesättigten cyclischen Ketonen

Country Status (2)

Country	Link
BE (1)	BE585463A (fr)
CH (1)	CH376495A (fr)

1958
- 1958-12-17 CH CH6741158A patent/CH376495A/de unknown
1959
- 1959-12-09 BE BE585463A patent/BE585463A/fr unknown

Also Published As

Publication number	Publication date
BE585463A (fr)	1960-06-09

Publication	Publication Date	Title
DE841913C (de)	1952-06-19	Verfahren zur Herstellung cyclischer 1, 2-Ketole mit 10í¬18 Ringgliedern
CH376495A (de)	1964-04-15	Verfahren zur Herstellung von ungesättigten cyclischen Ketonen
EP0093425B1 (fr)	1985-07-17	Cétones cycliques insaturées
DE574838C (de)	1933-04-22	Verfahren zur Darstellung von cyclischen Glykolen und ihren Derivaten bzw. von Ketonen
DE951811C (de)	1956-11-08	Verfahren zur Herstellung von Propiolsaeure
DE1104504B (de)	1961-04-13	Verfahren zur Herstellung von ungesaettigten cyclischen Ketonen
CH373373A (de)	1963-11-30	Verfahren zur Herstellung von ungesättigten Ketonen
DE870698C (de)	1953-03-16	Verfahren zur Herstellung von Hydrochinonen
US1644546A (en)	1927-10-04	Process for the manufacture of d.l.-nerolidol
DE1118191B (de)	1961-11-30	Verfahren zur Herstellung von ungesaettigten Ketonen
AT233540B (de)	1964-05-11	Verfahren zur Herstellung von Allenestern
DE965404C (de)	1957-06-06	Verfahren zur Herstellung von 2-Methylcyclopentandion-(1,3)
DE2201365A1 (de)	1972-09-07	Neuer alpha-Methyl-buttersaeureester
AT205962B (de)	1959-10-26	Verfahren zur Herstellung von neuen ungesättigten aliphatischen Amino-diolen
AT216156B (de)	1961-07-10	Verfahren zur Herstellung von Polyhydrophenanthren-Verbindungen
DE961258C (de)	1957-04-04	Verfahren zur Herstellung von Retrodehydropolyenaldehyden
DE855861C (de)	1952-11-17	Verfahren zur Herstellung von Dioxytetrahydrofuranen
DE960278C (de)	1957-03-21	Verfahren zur Herstellung von Cyclocitral
DE927268C (de)	1955-05-02	Verfahren zur Herstellung von Polyhydronaphthalinverbindungen
AT214432B (de)	1961-04-10	Verfahren zur Herstellung von Mono- und/oder Disubstitutionsprodukten der Dimethylbenzohydrochinone-(1,4) und den zugehörigen Chinonen
DE1109677B (de)	1961-06-29	Verfahren zur Herstellung von ungesaettigten Ketonen vom Jonontyp
CH373034A (de)	1963-11-15	Verfahren zur Herstellung von ungesättigten Ketonen
DE1092003B (de)	1960-11-03	Stereospezifisches Verfahren zur Herstellung von 1,3-Dihydroxy-2-amino-alkenen-4
DE1021360B (de)	1957-12-27	Verfahren zur Herstellung von Polyenaldehyden mit 19 Kohlenstoffatomen
DE1102716B (de)	1961-03-23	Verfahren zur Herstellung von 4-Cyclohexylbuten-(2)-al