GB760667A - Substituted tetrahydronaphthalenes - Google Patents
Substituted tetrahydronaphthalenesInfo
- Publication number
- GB760667A GB760667A GB35389/54A GB3538954A GB760667A GB 760667 A GB760667 A GB 760667A GB 35389/54 A GB35389/54 A GB 35389/54A GB 3538954 A GB3538954 A GB 3538954A GB 760667 A GB760667 A GB 760667A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetyl
- tetrahydronaphthalene
- ethyl
- chloride
- compounds
- 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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 239000002304 perfume Substances 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 239000000344 soap Substances 0.000 abstract 4
- HSTAGCWQAIXJQM-UHFFFAOYSA-N 2,5-dichloro-2,5-dimethylhexane Chemical compound CC(C)(Cl)CCC(C)(C)Cl HSTAGCWQAIXJQM-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000003921 oil Substances 0.000 abstract 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 2
- 239000012346 acetyl chloride Substances 0.000 abstract 2
- 239000002537 cosmetic Substances 0.000 abstract 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 2
- AISXBZVAYNUAKB-UHFFFAOYSA-N 1,1,4,4,6-pentamethyl-2,3-dihydronaphthalene Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C)=CC=2 AISXBZVAYNUAKB-UHFFFAOYSA-N 0.000 abstract 1
- QZADYGNSQCABPT-UHFFFAOYSA-N 1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethanone Chemical compound CC1(C)CCC(C)(C)C2=C1C=C(C)C(C(=O)C)=C2 QZADYGNSQCABPT-UHFFFAOYSA-N 0.000 abstract 1
- KSEZPRJUTHMFGZ-UHFFFAOYSA-N 1-(3-ethyl-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)ethanone Chemical compound CC1(C)CCC(C)(C)C2=C1C=C(C(C)=O)C(CC)=C2 KSEZPRJUTHMFGZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 241000402754 Erythranthe moschata Species 0.000 abstract 1
- -1 alkyl substituted benzene hydrocarbon Chemical class 0.000 abstract 1
- 235000013871 bee wax Nutrition 0.000 abstract 1
- 239000012166 beeswax Substances 0.000 abstract 1
- 229910021538 borax Inorganic materials 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N p-methylisopropylbenzene Natural products CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 abstract 1
- 235000010339 sodium tetraborate Nutrition 0.000 abstract 1
- 239000004328 sodium tetraborate Substances 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- JWJVZCNJVZZHMP-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1.CC(C)(C)C1=CC=CC=C1 JWJVZCNJVZZHMP-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Abstract
The invention comprises 6-(lower alkyl)-7-acetyl - 1,1,4,4 - tetramethyl - 1,2,3,4 - tetrahydronaphthalenes where the lower alkyl group contains 1 to 4 carbon atoms such as methyl, ethyl, isopropyl, or tertiary butyl. The compounds are prepared by condensing 2,5 - dichloro - 2,5 - dimethyl - hexane with a lower alkyl substituted benzene hydrocarbon in the presence of a condensing agent such as aluminium chloride or ferric chloride to form the 6 - (lower alkyl) - 1,1,4,4 - tetramethyl-1,2,3,4 - tetrahydronaphthalene which is then acetylated. In examples: (1) 2,5-dichloro-2,5-dimethylhexane is condensed with toluene in the presence of anhydrous aluminium chloride to give 1,1,4,4,6 - pentamethyl - 1,2,3,4-tetrahydronaphthalene which is further condensed with acetyl chloride in ethylene dichloride in the presence of anhydrous aluminium chloride to yield 7-acetyl-1,1,4,4,6-pentamethyl - 1,2,3,4 - tetrahydronaphthalene; (2) anhydrous ferric chloride is used to condense 2,5 - dichloro - 2,5 - dimethyl - hexane with ethyl benzene and the product is acetylated with acetyl chloride in ethylene dichloride using aluminium chloride to give 7-acetyl-1,1,4,4-tetramethyl - 6 - ethyl - 1,2,3,4 - tetrahydronaphthalene; (3) and (4) cumene and tertbutyl benzene replace toluene in (1) above to yield the 6-isopropyl- and 6-tert-butyl-homologues respectively. The compounds are synthetic musks for use in perfumes, cosmetics and soaps (see Groups III and VI).ALSO:Soap compositions are perfumed by addition of a 6 - alkyl - 7 - acetyl - 1:1:4:4 - tetramethyl - 1:2:3:4 -tetrahydronaphthalene in which the alkyl group contains from 1 to 4 carbon atoms and may be methyl, ethyl, isopropyl and tert - butyl. Examples are given.ALSO:Cosmetic perparations and perfumes containing synthetic musk-like compounds which are 6 - alkyl - 7 - acetyl - 1 : 1 : 4 : 4 - tetra methyl - 1 : 2 : 3 : 4 - tetrahydro - naphthalenes in which the alkyl group contains from 1 to 4 carbon atoms such as methyl, ethyl, isopropyl, and tertiarybutyl are described and claimed. In examples, (6), creams compounded from beeswax, mineral oil, borax, water and a perfume oil containing the above compounds are described; (7), floral soap perfume oils and (8) bouquet type soap perfume oils containing the above compounds are described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US760667XA | 1953-12-14 | 1953-12-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB760667A true GB760667A (en) | 1956-11-07 |
Family
ID=22129737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35389/54A Expired GB760667A (en) | 1953-12-14 | 1954-12-07 | Substituted tetrahydronaphthalenes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB760667A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040338A2 (en) * | 1978-04-19 | 1981-11-25 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Process for the preparation of acylated indanes and tetrahydronaphthalenes |
| EP0098546A1 (en) * | 1982-07-02 | 1984-01-18 | Fritzsche Dodge & Olcott Inc. | Novel aromatic musks |
| 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 |
-
1954
- 1954-12-07 GB GB35389/54A patent/GB760667A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040338A2 (en) * | 1978-04-19 | 1981-11-25 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Process for the preparation of acylated indanes and tetrahydronaphthalenes |
| EP0040338A3 (en) * | 1978-04-19 | 1981-12-02 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Process for the preparation of acylated indanes and tetrahydronaphthalenes |
| EP0098546A1 (en) * | 1982-07-02 | 1984-01-18 | Fritzsche Dodge & Olcott Inc. | Novel aromatic musks |
| 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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