GB1300970A - Indane compounds, processes of making same and their use as fragrance material - Google Patents

Indane compounds, processes of making same and their use as fragrance material

Info

Publication number
GB1300970A
GB1300970A GB37592/70A GB3759270A GB1300970A GB 1300970 A GB1300970 A GB 1300970A GB 37592/70 A GB37592/70 A GB 37592/70A GB 3759270 A GB3759270 A GB 3759270A GB 1300970 A GB1300970 A GB 1300970A
Authority
GB
United Kingdom
Prior art keywords
pentamethylindane
pentamethyl
compounds
tetrahydro
indanone
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
GB37592/70A
Inventor
John B Hall
Ernst Theodore Theimer
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.)
Internat Flavours & Fragrances
International Flavors and Fragrances Inc
Original Assignee
Internat Flavours & Fragrances
International Flavors and Fragrances Inc
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 Internat Flavours & Fragrances, International Flavors and Fragrances Inc filed Critical Internat Flavours & Fragrances
Publication of GB1300970A publication Critical patent/GB1300970A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0084—Antioxidants; Free-radical scavengers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
    • C07C13/465—Indenes; Completely or partially hydrogenated indenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of SO3H groups or a derivative thereof
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
    • 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
    • C07C45/511—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 singly bound oxygen functional groups to >C = O groups
    • C07C45/513—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 singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic
    • C07C49/423—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system
    • C07C49/427—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
    • C07C49/443—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing eight or nine carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
    • C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
    • C07C49/623—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
    • C07C49/633—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing eight or nine carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B9/00—Esters or ester-salts of leuco compounds of vat dyestuffs
    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/44—Perfumes; Colouring materials; Brightening agents ; Bleaching agents
    • C11D9/442—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Biochemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)

Abstract

1300970 Indane compounds and their use as fragrance materials INTERNATIONAL FLAVOURS & FRAGRANCES Inc 4 Aug 1970 [18 Aug 1969 (5)] 37592/70 Heading C2C [Also in Divisions A5 and C5] The invention comprises indane compounds of formula in which formulµ one of R 1 and R 2 is 0 and the other is hydrogen; R 6 is hydrogen, alkyl or an acyl group and R 3 is a carbonyl oxygen or a hydroxy, acyloxy or alkoxy group. The compounds of Formula I also include their 7,7aepoxy derivatives. These compounds may be prepared by (a) oxidizing atetrahydro-1,1,2,3,3- pentamethylindane with a hexavalent chromium oxidizing agent, (b) by reacting a 3a,7a-epoxyhexahydro - 1,1,2,3,3 - pentamethylindane with a trialkoxyaluminium, (c) by oxidizing a tetrahydro-1,1,2,3,3-pentamethylindane with a percarboxylic acid and obtaining a 3d,7d-epoxyhexahydropentamethylindane, (d) by treating 4d,7d - epoxyhexahydro - 1,1,2,3,3 - pentamethylindane with a strong protonic acid to form 4,5-dihydropentamethylindane, (e) by oxidizing a 1,1,2,3,3-pentamethylhexahydroindanol with a hexavalent chromium oxidizing agent to provide the corresponding ketone. The following compounds are prepared in the examples: 4,5,6,7 - tetrahydro - 1,1,2,3,3 - pentamethylindane; 6,7 - dihydro - 1,1,2,3,3 - pentamethyl-4(5H)-indanone; 7,7a-epoxy-5,6,7,7atetrahydro - 1,1,2,3,3 - pentamethyl - 4(3aH)- indanone; 5 - methoxy - 1,1,2,3,3 - pentamethylindane; 6,7 - dihydro - 1,1,2,3,3 - pentamethyl - 5(4H) - indanone and 7,7a - dihydro- 1,1,2,3,3 - pentamethyl - 5(6H) - indanone; 3a,7a - epoxyhexahydro - 1,1,2,3,3 - pentamethylindane; 4,5,6,7 - tetrahydro - 1,1,2,3,3- pentamethyl - 4 - indanol; methyl - 4,5,6,7- tetrahydro - 1,1,2,3,3 - pentamethyl - 4 - indanyl ether; 4,5,6,7 - tetrahydro - 1,1,2,3,3 - pentamethyl - 4 - indanyl acetate; 4,5 - dihydro- 1,1,2,3,3 - pentamethylindane; 1,1,2,3,3 - pentamethylhexahydroindan-5-ol and 1,1,2,3, 3-pentamethylhexahydroindan-4-ol. The compounds of the invention are reported to have a woody odour and may be incorporated as fragrances in soaps, solid, liquid detergents and cosmetics.
GB37592/70A 1969-08-18 1970-08-04 Indane compounds, processes of making same and their use as fragrance material Expired GB1300970A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US85107669A 1969-08-18 1969-08-18
US85104869A 1969-08-18 1969-08-18
US85108669A 1969-08-18 1969-08-18
US85109069A 1969-08-18 1969-08-18
US85104969A 1969-08-18 1969-08-18

Publications (1)

Publication Number Publication Date
GB1300970A true GB1300970A (en) 1972-12-29

Family

ID=27542261

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37592/70A Expired GB1300970A (en) 1969-08-18 1970-08-04 Indane compounds, processes of making same and their use as fragrance material

Country Status (8)

Country Link
BE (1) BE753751A (en)
CA (1) CA992549A (en)
CH (1) CH523962A (en)
DE (1) DE2036936B2 (en)
FR (1) FR2058364B1 (en)
GB (1) GB1300970A (en)
IT (1) IT1019005B (en)
NL (1) NL153171B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0154918A2 (en) * 1984-03-14 1985-09-18 INTERNATIONAL FLAVORS & FRAGRANCES INC. Tertiary pentamethylindanol derivatives and organoleptic uses thereof
EP0195975A2 (en) * 1985-03-25 1986-10-01 L. GIVAUDAN & CIE Société Anonyme Bicyclic ketone, process for its preparation and odoriferous and/or aromatization compositions containing this bicyclic ketone
EP0260585A2 (en) * 1986-09-18 1988-03-23 L. GIVAUDAN & CIE Société Anonyme Bicyclic ketones, method for their production and aroma and/or flavour compositions containing said ketones
EP0827945A1 (en) * 1996-09-06 1998-03-11 INTERNATIONAL FLAVORS & FRAGRANCES INC. Methyl substituted tetrahydroindane methyl enol ethers, perfumery uses thereof, processes for preparing same, and process intermediates therefor
EP2305628A2 (en) 2009-09-23 2011-04-06 International Flavors & Fragrances Inc. Allylic Oxidation Method for the Preparation of Fragrances using Metal-Organic Compounds and Gold Catalysts
CN113929564A (en) * 2021-09-14 2022-01-14 安徽金禾化学材料研究所有限公司 Method for preparing kestone spice
CN115385770A (en) * 2022-10-10 2022-11-25 安徽金禾化学材料研究所有限公司 Method for preparing 1,2, 3-pentamethyl-4, 5,6, 7-tetrahydroindane

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH625197A5 (en) * 1976-06-03 1981-09-15 Buskine Sa Process for preparing verbenone, myrtenal and pinocarveol
US4659509A (en) * 1984-04-27 1987-04-21 Kuraray Co., Ltd. Aroma composition
US4902840A (en) * 1989-04-28 1990-02-20 International Flavors And Fragrances Inc. Substituted tetrahydroindane derivatives and organoleptic uses of substituted tetrahydroindanes

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0154918A2 (en) * 1984-03-14 1985-09-18 INTERNATIONAL FLAVORS & FRAGRANCES INC. Tertiary pentamethylindanol derivatives and organoleptic uses thereof
EP0154918A3 (en) * 1984-03-14 1986-05-28 International Flavors & Fragrances Inc. Tertiary pentamethylindanol derivatives and organoleptic uses thereof
US5163453A (en) * 1985-03-25 1992-11-17 Givaudan Corporation 3,5,5,6,8,8,-hexamethyl-1,2,3,4,5,6,7,8,-octahydro-2-naphthalenone
EP0195975A3 (en) * 1985-03-25 1987-06-03 L. GIVAUDAN & CIE Société Anonyme Bicyclic ketone, process for its preparation and odoriferous and/or aromatization compositions containing this bicyclic ketone
EP0195975A2 (en) * 1985-03-25 1986-10-01 L. GIVAUDAN & CIE Société Anonyme Bicyclic ketone, process for its preparation and odoriferous and/or aromatization compositions containing this bicyclic ketone
EP0260585A2 (en) * 1986-09-18 1988-03-23 L. GIVAUDAN & CIE Société Anonyme Bicyclic ketones, method for their production and aroma and/or flavour compositions containing said ketones
EP0260585A3 (en) * 1986-09-18 1989-04-26 L. Givaudan & Cie Societe Anonyme Bicyclic ketones, method for their production and aroma and/or flavour compositions containing said ketones
EP0827945A1 (en) * 1996-09-06 1998-03-11 INTERNATIONAL FLAVORS & FRAGRANCES INC. Methyl substituted tetrahydroindane methyl enol ethers, perfumery uses thereof, processes for preparing same, and process intermediates therefor
EP2305628A2 (en) 2009-09-23 2011-04-06 International Flavors & Fragrances Inc. Allylic Oxidation Method for the Preparation of Fragrances using Metal-Organic Compounds and Gold Catalysts
CN113929564A (en) * 2021-09-14 2022-01-14 安徽金禾化学材料研究所有限公司 Method for preparing kestone spice
CN113929564B (en) * 2021-09-14 2023-10-03 安徽金禾化学材料研究所有限公司 Method for preparing spice kemesdone
CN115385770A (en) * 2022-10-10 2022-11-25 安徽金禾化学材料研究所有限公司 Method for preparing 1,2, 3-pentamethyl-4, 5,6, 7-tetrahydroindane
CN115385770B (en) * 2022-10-10 2023-10-03 安徽金禾化学材料研究所有限公司 Method for preparing 1,2, 3-pentamethyl-4, 5,6, 7-tetrahydroindane

Also Published As

Publication number Publication date
FR2058364B1 (en) 1973-01-12
BE753751A (en) 1971-01-22
DE2036936C3 (en) 1974-05-30
CH523962A (en) 1972-06-15
CA992549A (en) 1976-07-06
DE2036936B2 (en) 1973-10-25
FR2058364A1 (en) 1971-05-28
IT1019005B (en) 1977-11-10
DE2036936A1 (en) 1971-07-08
NL153171B (en) 1977-05-16
NL7012137A (en) 1971-02-22

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PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee