GB896039A - Method of producing derivatives of the 1,1-dimethyl-octahydronaphthalene series - Google Patents
Method of producing derivatives of the 1,1-dimethyl-octahydronaphthalene seriesInfo
- Publication number
- GB896039A GB896039A GB24524/59A GB2452459A GB896039A GB 896039 A GB896039 A GB 896039A GB 24524/59 A GB24524/59 A GB 24524/59A GB 2452459 A GB2452459 A GB 2452459A GB 896039 A GB896039 A GB 896039A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- octahydronaphthalene
- och3
- cyclised
- give
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/553—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings polycyclic
-
- 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
- C07C403/02—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 containing only carbon and hydrogen atoms
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O 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
- C07C45/61—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
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1 - 1-Dimethyl-octahydronaphthalene derivatives of formula <FORM:0896039/IV (b)/1> in which the broken lines indicate that a single double bond is present in one of the four positions shown are prepared by cyclising a compound of formula <FORM:0896039/IV (b)/2> wherein R2, R3 and R4 are hydrogen atoms o alkyl groups and R1 is a hydroxy, alkyl or alkoxy group or R1 is hydrogen and the compound is in the form of a Schiff's base, is cyclised with phosphoric acid or boron trifluoride, or mixtures thereof, at a temperature between -30 DEG C. and +75 DEG C. or with sulphuric acid and/or formic acid at a temperature between -30 DEG C. and +10 DEG C. The starting materials are obtained by a Diels-alder reaction between myrcene and an appropriate dienophile compound. The final products are odoriferous and may be used in perfumes. In examples: (1) myrcene and methyl acrylate are heated in the presence of phenyl-b -naphthylamine to give a starting material wherein R1=OCH3 and R2 to R4=H, which is cyclised with sulphuric acid, phosphoric acid or boron trifluoride to give 1 : 1-dimethyl-7-carbomethoxy - octahydronaphthalene and the starting materials and cyclised products wherein R1=CH3, R2=H, R3 and R4=CH3; R1=OCH3, R2=H, R3 and R4=CH3; R1=OCH3, R2=CH3, R3 and R4=H; R1=OH, R2=CH3, R3 and R4=H are similarly prepared: (2) the Schiff base (with aniline) of the starting material wherein R1 to R4=H is dissolved in benzene and heated with phosphoric acid to give 1 : 1-dimethyl-7-formyl-octahydronaphthalene.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB24524/59A GB896039A (en) | 1959-07-16 | 1959-07-16 | Method of producing derivatives of the 1,1-dimethyl-octahydronaphthalene series |
FR801485A FR1231995A (en) | 1959-07-16 | 1959-07-29 | Process for the preparation of derivatives of the dimethyl-1, 1-octahydronaphthalene series and products conforming to those obtained |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB24524/59A GB896039A (en) | 1959-07-16 | 1959-07-16 | Method of producing derivatives of the 1,1-dimethyl-octahydronaphthalene series |
Publications (1)
Publication Number | Publication Date |
---|---|
GB896039A true GB896039A (en) | 1962-05-09 |
Family
ID=10213015
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24524/59A Expired GB896039A (en) | 1959-07-16 | 1959-07-16 | Method of producing derivatives of the 1,1-dimethyl-octahydronaphthalene series |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB896039A (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4107208A (en) * | 1976-11-11 | 1978-08-15 | International Flavors & Fragrances Inc. | Tetramethyl-hexahydroacetonaphthones |
WO1982004249A1 (en) * | 1981-05-28 | 1982-12-09 | Dawson Glenn William | Derivatives of(e)-beta-farnesene useful in insect control |
JPS6193138A (en) * | 1973-02-27 | 1986-05-12 | インタ−ナシヨナル フレ−ヴア−ズ アンド フラグランスイ−ズ インコ−ポレ−テツド | Manufacture of octahydro-tetramethylacetonaphthone |
US5731283A (en) * | 1997-01-28 | 1998-03-24 | International Flavors & Fragrances Inc. | 1(4'-methylpentyl)-4-substituted ethylcyclohexane derivatives, organoleptic uses thereof, process for producing same, and process intermediates therefor |
US6114565A (en) * | 1999-09-03 | 2000-09-05 | Millennium Specialty Chemicals | Process for obtaining nitriles |
US6160182A (en) * | 1998-08-19 | 2000-12-12 | Millennium Specialty Chemicals | Process for obtaining mixtures of isomeric acyloctahydronaphthalenes |
US7557148B2 (en) | 2003-11-27 | 2009-07-07 | Chugoku Marine Paints, Ltd. | Cyclic carboxylic acid compound and use thereof |
US9181393B2 (en) | 2011-08-17 | 2015-11-10 | Dow Global Technologies, Llc | Biorenewable biodegradable surfactants |
-
1959
- 1959-07-16 GB GB24524/59A patent/GB896039A/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6193138A (en) * | 1973-02-27 | 1986-05-12 | インタ−ナシヨナル フレ−ヴア−ズ アンド フラグランスイ−ズ インコ−ポレ−テツド | Manufacture of octahydro-tetramethylacetonaphthone |
US4107208A (en) * | 1976-11-11 | 1978-08-15 | International Flavors & Fragrances Inc. | Tetramethyl-hexahydroacetonaphthones |
WO1982004249A1 (en) * | 1981-05-28 | 1982-12-09 | Dawson Glenn William | Derivatives of(e)-beta-farnesene useful in insect control |
US4546110A (en) * | 1981-05-28 | 1985-10-08 | National Research Development Corporation | Pheromones |
US5731283A (en) * | 1997-01-28 | 1998-03-24 | International Flavors & Fragrances Inc. | 1(4'-methylpentyl)-4-substituted ethylcyclohexane derivatives, organoleptic uses thereof, process for producing same, and process intermediates therefor |
US6160182A (en) * | 1998-08-19 | 2000-12-12 | Millennium Specialty Chemicals | Process for obtaining mixtures of isomeric acyloctahydronaphthalenes |
US6114565A (en) * | 1999-09-03 | 2000-09-05 | Millennium Specialty Chemicals | Process for obtaining nitriles |
US7557148B2 (en) | 2003-11-27 | 2009-07-07 | Chugoku Marine Paints, Ltd. | Cyclic carboxylic acid compound and use thereof |
US9181393B2 (en) | 2011-08-17 | 2015-11-10 | Dow Global Technologies, Llc | Biorenewable biodegradable surfactants |
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