CA1048058A - Oxobicyclo-14 (10.4.0) hexadec-1(12)ene, oxobicyclo-14 (10.4.0) hexadec-12 ene et oxobicyclo-14 (10.4.0) hexadecane - Google Patents

Oxobicyclo-14 (10.4.0) hexadec-1(12)ene, oxobicyclo-14 (10.4.0) hexadec-12 ene et oxobicyclo-14 (10.4.0) hexadecane

Info

Publication number: CA1048058A
Authority: CA; Canada
Prior art keywords: oxobicyclo; ene; hexadec; mixture; beta
Prior art date: 1974-04-08
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

Application number

CA197,085A

Other languages

English (en)

Other versions

CA197085S (en

Inventor

Seymour Lemberg

Audley L. Cain

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Stepan Co

Original Assignee

Stepan Chemical Co

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.)

1974-04-08

Filing date

1974-04-08

Publication date

1979-02-06

1974-04-08 Application filed by Stepan Chemical Co filed Critical Stepan Chemical Co

1974-04-08 Priority to CA197,085A priority Critical patent/CA1048058A/fr

1979-02-06 Application granted granted Critical

1979-02-06 Publication of CA1048058A publication Critical patent/CA1048058A/fr

Status Expired legal-status Critical Current

Links

QBODJFBDSXREQC-UHFFFAOYSA-N 2,4,5,6,7,8,9,10,11,12,13,14-dodecahydro-1H-benzo[12]annulen-3-one Chemical compound O=C1CC=2CCCCCCCCCCC2CC1 QBODJFBDSXREQC-UHFFFAOYSA-N 0.000 title claims abstract 7
OBRHPKKTTCLTFD-UHFFFAOYSA-N 2,5,6,7,8,9,10,11,12,13,14,14a-dodecahydro-1h-benzo[12]annulen-3-one Chemical compound C1CCCCCCCCCC2=CC(=O)CCC21 OBRHPKKTTCLTFD-UHFFFAOYSA-N 0.000 title claims abstract 5
ABCZRZONYUNVHN-UHFFFAOYSA-N 2,4,4a,5,6,7,8,9,10,11,12,13,14,14a-tetradecahydro-1h-benzo[12]annulen-3-one Chemical compound C1CCCCCCCCCC2CC(=O)CCC21 ABCZRZONYUNVHN-UHFFFAOYSA-N 0.000 title claims abstract 4
238000000034 method Methods 0.000 title description 9
238000002360 preparation method Methods 0.000 title description 3
239000000203 mixture Substances 0.000 claims abstract description 29
150000001875 compounds Chemical class 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 abstract description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract description 10
SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 abstract description 8
230000007062 hydrolysis Effects 0.000 abstract description 8
238000006460 hydrolysis reaction Methods 0.000 abstract description 8
241000402754 Erythranthe moschata Species 0.000 abstract description 7
239000003205 fragrance Substances 0.000 abstract description 7
125000005594 diketone group Chemical class 0.000 abstract description 6
238000005984 hydrogenation reaction Methods 0.000 abstract description 6
235000009508 confectionery Nutrition 0.000 abstract description 5
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract description 4
238000004821 distillation Methods 0.000 abstract description 4
238000007363 ring formation reaction Methods 0.000 abstract description 4
SZTBSJOMNRSBGA-MHWRWJLKSA-N 4-[(1e)-cyclododecen-1-yl]morpholine Chemical compound C1COCCN1C/1=C/CCCCCCCCCC\1 SZTBSJOMNRSBGA-MHWRWJLKSA-N 0.000 abstract 1
238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 abstract 1
239000002304 perfume Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000002585 base Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
150000002576 ketones Chemical class 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
SZTBSJOMNRSBGA-UHFFFAOYSA-N 4-(cyclododecen-1-yl)morpholine Chemical compound C1COCCN1C1=CCCCCCCCCCC1 SZTBSJOMNRSBGA-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
-1 alkali metal amide Chemical class 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229960000443 hydrochloric acid Drugs 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
WJVILXXPBCHQJM-UHFFFAOYSA-N 2-(3-oxobutyl)cyclododecan-1-one Chemical compound O=C(CCC1C(CCCCCCCCCC1)=O)C WJVILXXPBCHQJM-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 2
230000009965 odorless effect Effects 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
150000003431 steroids Chemical class 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
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
206010013647 Drowning Diseases 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
241000212342 Sium Species 0.000 description 1
GOLGRUQIRPJCMP-UHFFFAOYSA-N [C].[Cl].[Cl].[Cl].[Cl] Chemical compound [C].[Cl].[Cl].[Cl].[Cl] GOLGRUQIRPJCMP-UHFFFAOYSA-N 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical group O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000001914 filtration Methods 0.000 description 1
SIHWESHIQGPCBP-UHFFFAOYSA-N hexadec-4-ene Chemical class CCCCCCCCCCCC=CCCC SIHWESHIQGPCBP-UHFFFAOYSA-N 0.000 description 1
DCAYPVUWAIABOU-NJFSPNSNSA-N hexadecane Chemical class CCCCCCCCCCCCCCC[14CH3] DCAYPVUWAIABOU-NJFSPNSNSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA197,085A 1974-04-08 1974-04-08 Oxobicyclo-14 (10.4.0) hexadec-1(12)ene, oxobicyclo-14 (10.4.0) hexadec-12 ene et oxobicyclo-14 (10.4.0) hexadecane Expired CA1048058A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA197,085A CA1048058A (fr)	1974-04-08	1974-04-08	Oxobicyclo-14 (10.4.0) hexadec-1(12)ene, oxobicyclo-14 (10.4.0) hexadec-12 ene et oxobicyclo-14 (10.4.0) hexadecane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA197,085A CA1048058A (fr)	1974-04-08	1974-04-08	Oxobicyclo-14 (10.4.0) hexadec-1(12)ene, oxobicyclo-14 (10.4.0) hexadec-12 ene et oxobicyclo-14 (10.4.0) hexadecane

Publications (1)

Publication Number	Publication Date
CA1048058A true CA1048058A (fr)	1979-02-06

Family

ID=4099668

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA197,085A Expired CA1048058A (fr)	1974-04-08	1974-04-08	Oxobicyclo-14 (10.4.0) hexadec-1(12)ene, oxobicyclo-14 (10.4.0) hexadec-12 ene et oxobicyclo-14 (10.4.0) hexadecane

Country Status (1)

Country	Link
CA (1)	CA1048058A (fr)

1974
- 1974-04-08 CA CA197,085A patent/CA1048058A/fr not_active Expired

Publication	Publication Date	Title
EP0054410B1 (fr)	1984-10-03	Composition de parfum
Padwa et al.	1989	Intramolecular cyclopropanation reaction of furanyl diazo ketones
US3514489A (en)	1970-05-26	Sec-butyl cyclohexane carboxaldenhydes
Rao et al.	1979	Base-catalyzed autoxidation of cyclic ketones
Carre et al.	1984	Arynic condensation of ketone enolates. 16. Efficient access to a new series of benzocyclobutenols
US4948780A (en)	1990-08-14	Alcohols and ethers having cyclododecyl and cyclododecenyl groups, process for their preparation and scents containing same
RU2159758C2 (ru)	2000-11-27	Циклопентадиенильные производные и способы их получения
Yadav et al.	1997	Indium in organic synthesis: Convenient synthesis of β, γ-unsaturated ketones
US3981920A (en)	1976-09-21	Method for preparing cyclopentenone derivatives
US3487102A (en)	1969-12-30	Process for preparing alpha,3,3 - trimethyl cyclohexane methyl alkanoates
US4045489A (en)	1977-08-30	Process for producing cis-jasmone
Cope et al.	1957	Proximity Effects. IX. Solvolysis of trans-Cycloöctene Oxide
US3057888A (en)	1962-10-09	Processes for and intermediates in the manufacture of unsaturated aldehydes and ketones
EP0033959B1 (fr)	1983-05-11	Composé spirannique insaturé, son utilisation dans les parfums et les aromes et procédé pour sa préparation
US3816534A (en)	1974-06-11	14-oxobicyclo(10.4.0)hexadec-1(12)-ene,14-oxobicyclo(10.4.0)hexadec-12-ene,14-oxobicyclo(10.4.0)-hexadecane and process for their preparation
Gaoni et al.	1966	Ring Cleavage and Oxidation Reactions of Dimethyldimedone
US4918052A (en)	1990-04-17	Perfume base composition
US4722808A (en)	1988-02-02	Use of cyclododecenylacetonitrile as a fragrance component
CA1238332A (fr)	1988-06-21	Derives de dihydrofurane utiles comme parfums synthetiques; methode de preparation
US4992416A (en)	1991-02-12	Isomeric formyl trimethylbicyclo[2.2.2]oct-7-enes
US6118027A (en)	2000-09-12	Preparation of unsaturated aldehydes from propargyl alcohol and conjugated diolefins
US4424146A (en)	1984-01-03	Acetaldehyde ethyl 6-dihydrolinalyl acetal perfume compositions
US5191125A (en)	1993-03-02	Procedure for the preparation of bicyclo [3.2.0]hept-2-en-7-ones
CH618672A5 (fr)	1980-08-15
US3470241A (en)	1969-09-30	Cyclopropane intermediates for irones