GB787541A - Substituted tetrahydronaphthalenes - Google Patents
Substituted tetrahydronaphthalenesInfo
- Publication number
- GB787541A GB787541A GB172/56A GB17256A GB787541A GB 787541 A GB787541 A GB 787541A GB 172/56 A GB172/56 A GB 172/56A GB 17256 A GB17256 A GB 17256A GB 787541 A GB787541 A GB 787541A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetyl
- tetrahydro
- phenyl
- compound
- composition
- 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
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- RICANWQLSTZRFD-UHFFFAOYSA-N 1-(5,5,6,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethanone Chemical class CC(=O)C1=CC=C2C(C)(C)C(C)CC(C)(C)C2=C1 RICANWQLSTZRFD-UHFFFAOYSA-N 0.000 abstract 2
- GKSJXWYSYWFBEY-UHFFFAOYSA-N 2,2,5,5-tetramethyloxolan-3-ol Chemical compound CC1(C)CC(O)C(C)(C)O1 GKSJXWYSYWFBEY-UHFFFAOYSA-N 0.000 abstract 2
- DNRJTBAOUJJKDY-UHFFFAOYSA-N 2-Acetyl-3,5,5,6,8,8-hexamethyl-5,6,7,8- tetrahydronaphthalene Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)C(C)CC(C)(C)C2=C1 DNRJTBAOUJJKDY-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- VLKFGNVVNLUROM-UHFFFAOYSA-N 1,1,2,4,4-pentamethyl-2,3-dihydronaphthalene Chemical compound C1=CC=C2C(C)(C)C(C)CC(C)(C)C2=C1 VLKFGNVVNLUROM-UHFFFAOYSA-N 0.000 abstract 1
- HWFLEGUPVIFSJN-UHFFFAOYSA-N 2,2,5,5-tetramethyloxolan-3-one Chemical compound CC1(C)CC(=O)C(C)(C)O1 HWFLEGUPVIFSJN-UHFFFAOYSA-N 0.000 abstract 1
- NLVRHMBZQAMXBX-UHFFFAOYSA-N 2,4,5-trimethylhex-4-en-2-ylbenzene Chemical compound CC(C)=C(CC(C)(C1=CC=CC=C1)C)C NLVRHMBZQAMXBX-UHFFFAOYSA-N 0.000 abstract 1
- ASWPPZVTWXWGFU-UHFFFAOYSA-N 2,5-dimethyl-5-phenylhexan-3-one Chemical compound CC(C)C(=O)CC(C)(C)C1=CC=CC=C1 ASWPPZVTWXWGFU-UHFFFAOYSA-N 0.000 abstract 1
- VEHLNEQZMGSTKG-UHFFFAOYSA-N 2,5-dimethyl-5-phenylhexane-2,3-diol Chemical compound CC(C)(C(CC(C)(C1=CC=CC=C1)C)O)O VEHLNEQZMGSTKG-UHFFFAOYSA-N 0.000 abstract 1
- HWOXCCZQFUDKAU-UHFFFAOYSA-N CC(C)C(CC(C)(C1=CC=CC=C1)C)(O)C Chemical compound CC(C)C(CC(C)(C1=CC=CC=C1)C)(O)C HWOXCCZQFUDKAU-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 238000003747 Grignard reaction Methods 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
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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
- C11B9/0053—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms both rings being six-membered
Abstract
The invention comprises (1) a composition consisting of a mixture of 6-acetyl- and 7-acetyl-1,1,3,4,4 - pentamethyl - 1,2,3,4 - tetrahydro - naphthalenes, (2) the compound 7-acetyl-1,1,3,4,4,6 - hexamethyl - 1,2,3,4 - tetrahydro - naphthalene, and (3) the preparation of this composition and of this compound. The composition is prepared by reacting benzene with 2,2,5,5-tetramethyl tetrahydro-3-furanol in presence of a Friedel-Crafts catalyst, e.g. AlCl3, to form 2,5-dimethyl - 5 - phenyl - 2,3 - hexanediol, dehydrating this with sulphuric acid, effecting a Grignard reaction with methyl magnesium iodide on the resulting 2,5 - dimethyl - 5 - phenyl - 3 - hexanone to form 2,3,5 - trimethyl - 5 - phenyl - 3 - hexanol, dehydrating this in the presence of p-toluene sulphonic acid to form 2,3,5-trimethyl-5-phenyl-2-hexene, cyclizing this in the presence of a cyclizing agent such as sulphuric acid, and acetylating, e.g. with acetyl chloride, the resulting 1,1,3,4,4 - pentamethyl - 1,2,3,4 - tetrahydro - naphthalene. The 7-acetyl hexamethyl compound is prepared similarly from toluene. Examples are given. Starting material. 2,2,5,5 - Tetramethyl tetrahydro-3-furanol is prepared by catalytic hydrogenation of 2,2,5,5-tetramethyltetrahydro-3-furanone.ALSO:Soaps contain the musk-like composition, a mixture of 6- and 7-acetyl-1,1,3,4,4-pentamethyl - 1,2,3,4 - tetrahydronaphthalenes, or the musk-like compound, 7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US787541XA | 1955-02-23 | 1955-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB787541A true GB787541A (en) | 1957-12-11 |
Family
ID=22146024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB172/56A Expired GB787541A (en) | 1955-02-23 | 1956-01-03 | Substituted tetrahydronaphthalenes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB787541A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5162588A (en) * | 1989-06-30 | 1992-11-10 | Firmenich S.A. | Aromatic compounds, a process for preparation thereof and use of same as perfuming ingredients |
| US5185318A (en) * | 1989-06-30 | 1993-02-09 | Firmenich S.A. | Aromatic compounds, a process for preparation thereof and use of same as perfuming ingredients |
-
1956
- 1956-01-03 GB GB172/56A patent/GB787541A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5162588A (en) * | 1989-06-30 | 1992-11-10 | Firmenich S.A. | Aromatic compounds, a process for preparation thereof and use of same as perfuming ingredients |
| US5185318A (en) * | 1989-06-30 | 1993-02-09 | Firmenich S.A. | Aromatic compounds, a process for preparation thereof and use of same as perfuming ingredients |
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