NL8302763A - Werkwijze ter bereiding van 4-methyljonon. - Google Patents

Werkwijze ter bereiding van 4-methyljonon. Download PDF

Info

Publication number: NL8302763A
Authority: NL; Netherlands
Prior art keywords: change; line; methyl; trimethyl; reaction
Prior art date: 1983-07-28

Application number

NL8302763A

Other languages

English (en)

Dutch (nl)

Original Assignee

Inst Khim Akademii Nauk Estons

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.)

1983-07-28

Filing date

1983-08-04

Publication date

1985-03-01

1983-08-04 Application filed by Inst Khim Akademii Nauk Estons filed Critical Inst Khim Akademii Nauk Estons

1985-03-01 Publication of NL8302763A publication Critical patent/NL8302763A/nl

Links

238000004519 manufacturing process Methods 0.000 title claims 2
238000000034 method Methods 0.000 claims description 30
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 22
XBEDXFHHUBZRPT-UHFFFAOYSA-N 1-chloro-3,5,7-trimethylocta-2,6-diene Chemical compound CC(C)=CC(C)CC(C)=CCCl XBEDXFHHUBZRPT-UHFFFAOYSA-N 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 14
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 10
YZOPWNASQGPFJR-UHFFFAOYSA-N 2-chlorohex-2-ene Chemical compound CCCC=C(C)Cl YZOPWNASQGPFJR-UHFFFAOYSA-N 0.000 claims description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
239000004312 hexamethylene tetramine Substances 0.000 claims description 7
235000010299 hexamethylene tetramine Nutrition 0.000 claims description 7
229960004011 methenamine Drugs 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
MEUYRZMKJNIRNB-UHFFFAOYSA-N 3,5,7-trimethylocta-2,6-dienal Chemical compound CC(C)=CC(C)CC(C)=CC=O MEUYRZMKJNIRNB-UHFFFAOYSA-N 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 5
239000003208 petroleum Substances 0.000 claims description 5
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 5
239000011592 zinc chloride Substances 0.000 claims description 5
235000005074 zinc chloride Nutrition 0.000 claims description 5
229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
-1 methyl halogen Chemical class 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
238000006007 Sommelet synthesis reaction Methods 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
239000002966 varnish Substances 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 2
SPHLZZZXIWUZNM-UHFFFAOYSA-N 7,11-dimethyldodeca-4,6,10-trien-3-one Chemical compound CCC(=O)C=CC=C(C)CCC=C(C)C SPHLZZZXIWUZNM-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
238000003756 stirring Methods 0.000 description 10
238000002360 preparation method Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000012044 organic layer Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000003205 fragrance Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
AOWPVIWVMWUSBD-RNFRBKRXSA-N [(3r)-3-hydroxybutyl] (3r)-3-hydroxybutanoate Chemical compound C[C@@H](O)CCOC(=O)C[C@@H](C)O AOWPVIWVMWUSBD-RNFRBKRXSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000002360 explosive Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical compound CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-N 0.000 description 1
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
XSVRFEQHOVNWLG-UHFFFAOYSA-N 2-bromohex-2-ene Chemical compound CCCC=C(C)Br XSVRFEQHOVNWLG-UHFFFAOYSA-N 0.000 description 1
SUBNDNOQXVTHOF-UHFFFAOYSA-N 4,6-dimethylhept-5-en-2-one Chemical compound CC(=O)CC(C)C=C(C)C SUBNDNOQXVTHOF-UHFFFAOYSA-N 0.000 description 1
BOXWYTNXMPZDFX-UHFFFAOYSA-N 4-bromo-2-methylpent-2-ene Chemical compound CC(Br)C=C(C)C BOXWYTNXMPZDFX-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
JZQOJFLIJNRDHK-CMDGGOBGSA-N alpha-irone Chemical compound CC1CC=C(C)C(\C=C\C(C)=O)C1(C)C JZQOJFLIJNRDHK-CMDGGOBGSA-N 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000003845 household chemical Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229930002839 ionone Natural products 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000565 sealant Substances 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
- 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)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL8302763A 1983-07-28 1983-08-04 Werkwijze ter bereiding van 4-methyljonon. NL8302763A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3327304A DE3327304C2 (de)	1983-07-28	1983-07-28	Verfahren zur Herstellung von 4-Methyljonon
DE3327304		1983-07-28

Publications (1)

Publication Number	Publication Date
NL8302763A true NL8302763A (nl)	1985-03-01

Family

ID=6205179

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8302763A NL8302763A (nl)	1983-07-28	1983-08-04	Werkwijze ter bereiding van 4-methyljonon.

Country Status (6)

Country	Link
AT (1)	AT382867B (de)
CH (1)	CH655099A5 (de)
DE (1)	DE3327304C2 (de)
FR (1)	FR2550790B1 (de)
GB (1)	GB2144118B (de)
NL (1)	NL8302763A (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3233712A1 (de) *	1981-02-27	1983-03-10	Immanuel Roennow	Verkaufspackung fuer leichte kleidungsstuecke, insbesondere waeschestuecke oder andere leichte markenartikel fuer den persoenlichen gebrauch
EP0210391A1 (de) *	1985-06-24	1987-02-04	L. GIVAUDAN & CIE Société Anonyme	Verfahren zur Herstellung von cyclischen Verbindungen
JPS62178539A (ja) *	1986-01-31	1987-08-05	Kuraray Co Ltd	α，β−不飽和ケトン誘導体及びそれを含有する香料組成物

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR18508E (fr) *	1912-03-07	1914-05-13	Fabriques De Produits De Chimie Organique De Laire	Transformation de dérivés halogénés
DE933149C (de) *	1946-10-21	1955-09-22	Firmenich & Co	Verfahren zur Herstellung von 6-Methyl-ª‡-jononen und 6-Methyl-ª‰-jonon
NL69166C (de) *	1948-02-05
CH337522A (de) *	1955-09-06	1959-04-15	Hoffmann La Roche	Verfahren zur Herstellung von ungesättigten Ketonen
US2877271A (en) *	1957-11-27	1959-03-10	Hoffmann La Roche	Preparation of ionones by cyclization of pseudoionones with sulfuric acid
BE791528A (fr) *	1971-11-17	1973-05-17	Basf Ag	Procede de preparation d'aldehydes a liaison alpha, beta ethylenique, de poids moleculaire eleve
US3813450A (en) *	1972-02-11	1974-05-28	Universal Oil Prod Co	Preparation of geranyl compounds

1983
- 1983-07-22 AT AT0268983A patent/AT382867B/de not_active IP Right Cessation
- 1983-07-26 CH CH4101/83A patent/CH655099A5/de not_active IP Right Cessation
- 1983-07-27 GB GB08320207A patent/GB2144118B/en not_active Expired
- 1983-07-28 DE DE3327304A patent/DE3327304C2/de not_active Expired
- 1983-08-04 NL NL8302763A patent/NL8302763A/nl not_active Application Discontinuation
- 1983-08-18 FR FR8313454A patent/FR2550790B1/fr not_active Expired

Also Published As

Publication number	Publication date
FR2550790A1 (fr)	1985-02-22
FR2550790B1 (fr)	1987-09-25
ATA268983A (de)	1986-09-15
GB2144118B (en)	1987-04-29
GB8320207D0 (en)	1983-09-01
CH655099A5 (de)	1986-03-27
GB2144118A (en)	1985-02-27
DE3327304A1 (de)	1985-02-07
DE3327304C2 (de)	1987-04-02
AT382867B (de)	1987-04-27

Legal Events

Date	Code	Title
1986-07-01	BA	A request for search or an international-type search has been filed
1986-11-03	BB	A search report has been drawn up
1987-03-02	BC	A request for examination has been filed
1993-04-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US4010213A (en)	1977-03-01	Novel odorants
JP2011526252A (ja)	2011-10-06	匂い物質として適するイソロンギホラニル誘導体
EP0466019B1 (de)	1995-03-22	Dihydro-Campholen-Aldehydderivate
US4097531A (en)	1978-06-27	Substituted cyclopropane process and product
CN101415665A (zh)	2009-04-22	由叔萜烯醇制备的香料组合物
US3996290A (en)	1976-12-07	2,4-Dimethyl-2-phenyl-4-pentenal
US3845133A (en)	1974-10-29	Alicyclic diketones and process for their manufacture
US4014938A (en)	1977-03-29	4-Tricyclo[5,2,1,02,6 ]decyl-8-butanal
US3670026A (en)	1972-06-13	Unsaturated hydroxy ketones
US3812059A (en)	1974-05-21	Perfume compositions containing 6-propyl-3-cyclohexene carbaldehydes
CH644341A5 (fr)	1984-07-31	Composes tricycliques hydroxyles et leur utilisation en tant qu'ingredients parfumants.
CH639057A5 (fr)	1983-10-31	Aldehyde tricyclique alpha,beta-insature.
JP4676880B2 (ja)	2011-04-27	シクロオクト−（エン−）イル誘導体の香料としての使用
US4292244A (en)	1981-09-29	Novel 2,4-disubstituted pyran derivatives, their preparation and their use as scents
US3906047A (en)	1975-09-16	8-(2,6,6-Trimethyl-4-oxo-2-cyclohexen-1-ylidene-2-methylene-6-methyl-4,6-octadien-3-ol
US3470241A (en)	1969-09-30	Cyclopropane intermediates for irones
US3413351A (en)	1968-11-26	1, 1-dimethyl-2-(3-oxo-butyl-1) cyclopropane
US5892104A (en)	1999-04-06	Cycloheptenols and their derivatives, methods of making thereof, and utilization thereof as fragrances
Gil et al.	1996	Sex pheromone of Chilo Suppressalis: efficient syntheses of (Z)-11-hexadecenal,(Z)-13-octadecenal and (Z)-9-hexadecenal
Kraft et al.	1999	Synthesis of a constitutional isomer of nerol by consecutive Ireland–Claisen and Cope rearrangements
US4444982A (en)	1984-04-24	(+)- Or (-)-7-hydroxymethyl-2,6,6-trimethyltricyclo[6,2,1,01,5 ]undecane
US5023232A (en)	1991-06-11	Mixtures of bicyclic ethers and fragrance compositions containing same
RU2058287C1 (ru)	1996-04-20	2,8-диметил-5-оксанон-1(2)-ен-8-ол в виде смеси изомеров в качестве компонента парфюмерных композиций и способ его получения
US3729514A (en)	1973-04-24	Novel chemical compounds and process
AU731928B2 (en)	2001-04-05	Thiamacrolides