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GB896039A - Method of producing derivatives of the 1,1-dimethyl-octahydronaphthalene series - Google Patents

Method of producing derivatives of the 1,1-dimethyl-octahydronaphthalene series

Info

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
Application number
GB24524/59A
Inventor
Guenther Ohloff
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.)
Dragoco Gerberding and Co GmbH
Original Assignee
Dragoco Gerberding and Co GmbH
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.)
Filing date
Publication date
Application filed by Dragoco Gerberding and Co GmbH filed Critical Dragoco Gerberding and Co GmbH
Priority to GB24524/59A priority Critical patent/GB896039A/en
Priority to FR801485A priority patent/FR1231995A/en
Publication of GB896039A publication Critical patent/GB896039A/en
Expired legal-status Critical Current

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.
GB24524/59A 1959-07-16 1959-07-16 Method of producing derivatives of the 1,1-dimethyl-octahydronaphthalene series Expired GB896039A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (9)

* Cited by examiner, † Cited by third party
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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