GB796129A - Polyalkylindane derivatives and process for manufacturing the same - Google Patents
Polyalkylindane derivatives and process for manufacturing the sameInfo
- Publication number
- GB796129A GB796129A GB29268/54A GB2926854A GB796129A GB 796129 A GB796129 A GB 796129A GB 29268/54 A GB29268/54 A GB 29268/54A GB 2926854 A GB2926854 A GB 2926854A GB 796129 A GB796129 A GB 796129A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetyl
- indane
- ethyl
- formyl
- 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
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises carbonyl derivatives of polyalkyl indanes in which 4-6 of the hydrogen atoms of the five-membered ring are substituted by alkyl groups containing 1-3 carbon atoms and a carbonyl group containing 1-3 carbon atoms is substituted on the benzene ring. Preferred compounds also contain an alkyl group having 1-3 carbon atoms substituted on the benzene ring. The compounds are prepared by introducing a formyl, acetyl or propionyl group into the corresponding polyalkylindanes, which are prepared by the process described in Specification 796,130 (i.e. by the reaction of styrene hydrocarbons with alkenes in the presence of a catalyst). The formyl compounds may be prepared by introducing a chloromethyl group into the polyalkylindane by reaction thereof with paraformaldehyde and hydrogen chloride in the presence of zinc chloride as a catalyst, and then converting the chloromethyl group into a formyl group by reaction with (a) hexamethylene tetramine in aqueous acetic acid or (b) the sodium salt of 2-nitropropane in ethanol. alternatively the polyalkylindane may be treated by the Gattermann-Koch method to introduce the formyl group. The acetyl and propionyl compounds may be prepared by reacting the polyalkylindane with an acetyl or propionyl halide or with acetic or propionic acid anhydride in the presence of a FriedelCrafts catalyst, such as aluminium chloride. The compounds are used as musk odorants and the intensity of the odour increases with the number of alkyl substitutents in the fivemembered ring. In examples: (1) p-a -dimethylstyrene is reacted with tetramethylethene (or 2:3-dimethylbutene-1) in a mixture of acetic and sulphuric acids to give 1 : 1 : 2 : 2 : 3 : 3 : 5-heptamethylindane which is reacted with acetyl or propionyl chloride in the presence of aluminium chloride to give acetyl- or propionyl-1: 1 : 2 : 2 : 3 : 3 : 5-heptamethyl-indane; (2) as in (1) but starting with p-ethyl-a -methylstyrene, acetyl - 1 : 1 : 2 : 2 : 3 : 3 - hexamethyl-5-ethyl-indane is obtained; (3) 1 : 1 : 2 : 3 : 3 : 5-hexamethylindane is obtained as in (1) but using trimethylethene, then reacted with paraformaldehyde, hydrogen chloride and zinc chloride to give 6-chloromethyl-1 : 1 : 2 : 3 : 3 : 5-hexamethylindane which is treated with a mixture of sodium hydroxide, 2-nitropropane and ethanol to give 6-formyl-1 : 1 : 2 : 3 : 3 : 5-hexamethylindane; (4) 1 : 1 : 2 : 2 : 3 : 3 : 5-heotamethyl-indane is treated as in (3) to give the chloromethyl compound which is reacted with hexamethylenetetramine in aqueous acetic acid to give 6-formyl-1 : 1 : 2 : 2 : 3 : 3 : 5-heptamethylindane. In Table the following additional compounds are specified: acetyl-1 : 2 : 3 : 3 : 5-or -1 : 1 : 3 : 3 : 5- or 1 : 1 : 2 : 3 : 3-pentamethylindane, acetyl - 1 : 1 : 3 : 5 - tetramethyl - 3 - ethyl-or -isopropyl-indane, acetyl-1 : 1 : 5-trimethyl - 3 : 3 - diethyl - indane, acetyl - 1 : 1 : 3 : 3 - tetramethyl - 5 - ethyl - indane, acetyl - 1 : 1 : 3 : 3 : 3 : 5 - or 1 : 1 : 2 : 2 : 3 : 3-hexamethyl-indane, acetyl-1 : 1 : 2 : 3 : 5-pentamethyl - 3 - ethyl - indane, acetyl - 1 : 1 : 2 : 3 : 3-pentamethyl - 5 - ethyl - indane, acetyl - 1 : 1 : 3 : 3 : 5 - pentamethyl - 2 - ethyl - indane, a mixture of acetyl-1 : 1 : 2 : 2 : 3 : 5-hexamethyl-3 - ethyl - indane and acetyl - 1 : 1 : 2 : 3 : 3 : 5-hexamethyl - 2 8 ethyl - indane, acetyl - 1 : 1 : 3 : 3 - tetramethylindane and 6 - formyl-1 : 1 : 2 : 3 : 3-pentamethylindane.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US796129XA | 1953-10-09 | 1953-10-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB796129A true GB796129A (en) | 1958-06-04 |
Family
ID=22151651
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB29268/54A Expired GB796129A (en) | 1953-10-09 | 1954-10-11 | Polyalkylindane derivatives and process for manufacturing the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB796129A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3393994A (en) * | 1964-09-28 | 1968-07-23 | Givaudan Corp | Method of controlling weeds |
US4352748A (en) | 1977-02-25 | 1982-10-05 | Naarden International N.V. | Novel acyl-polyalkylindan compounds and the use thereof as a base for perfume, as well as perfume compositions |
US4440966A (en) * | 1981-03-13 | 1984-04-03 | Bush Boake Allen | Production of indanes |
-
1954
- 1954-10-11 GB GB29268/54A patent/GB796129A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3393994A (en) * | 1964-09-28 | 1968-07-23 | Givaudan Corp | Method of controlling weeds |
US4352748A (en) | 1977-02-25 | 1982-10-05 | Naarden International N.V. | Novel acyl-polyalkylindan compounds and the use thereof as a base for perfume, as well as perfume compositions |
US4440966A (en) * | 1981-03-13 | 1984-04-03 | Bush Boake Allen | Production of indanes |
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