GB796586A - Improvements in and relating to alkyl substituted acetyl indanes - Google Patents
Improvements in and relating to alkyl substituted acetyl indanesInfo
- Publication number
- GB796586A GB796586A GB170/56A GB17056A GB796586A GB 796586 A GB796586 A GB 796586A GB 170/56 A GB170/56 A GB 170/56A GB 17056 A GB17056 A GB 17056A GB 796586 A GB796586 A GB 796586A
- Authority
- GB
- United Kingdom
- Prior art keywords
- indane
- give
- acetyl
- ethyl
- pentamethyl
- 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
- ZDDDIYOBAOJYAZ-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)ethanone Chemical class C1=CC=C2C(C(=O)C)CCC2=C1 ZDDDIYOBAOJYAZ-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 title 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 abstract 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 5
- 235000011149 sulphuric acid Nutrition 0.000 abstract 5
- 239000001117 sulphuric acid Substances 0.000 abstract 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- QZRGDINMCFJQNO-UHFFFAOYSA-N 4-methyl-4-(4-methylphenyl)pentan-2-one Chemical compound CC(=O)CC(C)(C)C1=CC=C(C)C=C1 QZRGDINMCFJQNO-UHFFFAOYSA-N 0.000 abstract 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 abstract 1
- SLUYZNSVIZEKHX-UHFFFAOYSA-N 3,3-dimethyl-4-(4-methylphenyl)pentan-2-ol Chemical compound CC(C(C)O)(C(C)C1=CC=C(C=C1)C)C SLUYZNSVIZEKHX-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 abstract 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 abstract 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 abstract 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
- C11B9/0042—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
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
Abstract
The invention comprises 1 : 1 : 2 : 2 : 3 : 3 : 5-heptamethyl-6-acetyl-indane, 1 : 1 : 2 : 3 : 3 : 5-hexamethyl - 2 - ethyl - 6 - acetyl - indane, 1 : 1 : 3 : 3 : 5 - pentamethyl - 6 - acetyl - indane and 1 : 1 : 3 : 5 - tetramethyl - 3 - ethyl - 6 - acetyl-indane. The compounds have musklike odours. In examples: (1) p-cymene was condensed with isobutene in the presence of sulphuric acid to give 1 : 1 : 3 : 3 : 5-pentamethylindane which was acetylated with acetyl chloride in the presence of aluminium chloride and ethylene dichloride to give 1 : 1 : 3 : 3 : 5-pentamethyl-6-acetyl-indane; (2) toluene was condensed with mesityl oxide in the presence of aluminium chloride to give 4-methyl-4-p-tolyl-pentan-2-one which was reacted with methyl magnesium iodide to give 2 : 4 dimethyl-4-p-tolyl-pentan-2-ol which was cyclized with sulphuric acid to give 1:1:3:3:5-pentamethyl-indane which was nitrated to give 4:6-dinitro-1:1:3:3:5-pentamethyl-indane and acetylated as in (1) to give 1:1:3:3:5 - pentamethyl - 6 - acetyl - indane; (3) 4-methyl-4-p-tolyl-pentan-2-one obtained as in (2) was reacted with ethyl magnesium bromide to give 3:5-dimethyl-5-p-tolyl-hexan-3-ol which was cyclized with sulphuric acid to give 1:1:3:5-tetramethyl-3-ethyl-indane which was acetylated as in (1) to give 1:1:3:5 - tetramethyl - 3 - ethyl - 6 - acetyl-indane; (4) p-cymene was condensed with 2:3-dimethyl-butan-2-ol in the presence of sulphuric acid to give 1:1:2:2:3:3:5-heptamethyl-indane which was acetylated as in (1) to give 1:1:2:2:3:3:5-heptamethyl-6-acetyl-indane; (5) p-cymene was condensed with 2:3 - dimethyl - pentan - 2 - ol in the presence of sulphuric acid to give 1:1:2:3:3: 5-hexamethyl-2-ethyl-indane which was acetylated as in (1) to give 1:1:2:3:3:5-hexamethyl - 2 - ethyl - 6 - acetyl - indane, some of the 1:1:2:2:3:5 - hexamethyl - 3 - ethyl - isomer probably being present.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US796586XA | 1955-02-14 | 1955-02-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB796586A true GB796586A (en) | 1958-06-18 |
Family
ID=22151969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB170/56A Expired GB796586A (en) | 1955-02-14 | 1956-01-03 | Improvements in and relating to alkyl substituted acetyl indanes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB796586A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3509215A (en) * | 1967-06-15 | 1970-04-28 | Givaudan Corp | Acyl indan compounds |
-
1956
- 1956-01-03 GB GB170/56A patent/GB796586A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3509215A (en) * | 1967-06-15 | 1970-04-28 | Givaudan Corp | Acyl indan compounds |
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