US4077996A
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Process for the preparation of trans-deca hydronaphthalene derivatives
Assignee: Bayer Pharma AG
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Filing: 1976-04-14
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Granted: 1978-03-07
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Expires: 1996-04-14
Abstract
Abstract A process for the preparation of trans-decahydronaphthalene compounds of Formula I ##STR1## wherein X is lower alkyl, --(CH 2 ) 3 --Z--R 2 , ##STR2## --(CH 2 ) 3 COOR 4 , or --(CH 2 ) 3 CN; Y and Z are ketalized carbonyl or free, esterified, or etherified hydroxymethylene; U is halogen; R 1 , r 2 , and R 3 are lower alkyl; and R 4 is alkyl; Wherein an octahydronaphthalene compound of Formula II ##STR3## is converted, in the presence of bases, by reaction of a trialkyl chlorosilane of the formula (R.sub.5).sub.3 Si--Cl wherein the R 5 each are lower alkyl group, to a hexahydronaphthalene compound of the formula ##STR4## The hexahydronaphthalene compound is hydrogenated, in an inert solvent with hydrogen in the presence of a platinum-, palladium-, or rhodium-containing hydrogenation catalyst, to an octahydronaphthalene compound of the formula ##STR5## and a vinyl ketone of the formula XCOCH═CH.sub.2 is added to the thus-obtained octahydronaphthalene compound in an inert solvent in the presence of a Lewis acid.
Inventors
- 👤 Gerhard Sauer
- 👤 Ulrich Eder
- 👤 Gregor Haffer
- 👤 Gunter Neef
- 👤 Rudolf Wiechert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 20:11
CPC Classifications
C; C07; C07D; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D317/50; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
222 words
A process for preparing a trans-decahydronaphthalene compound of the formula ##STR13## wherein X is alkyl of 1-4 carbon atoms, --(CH 2 ) 3 --Z--R 2 ##STR14## --(CH 2 ) 3 COOR 4 , or --(CH 2 ) 3 CN; Y and Z are alkylenedioxymethylene of up to 6 carbon atoms in the alkylene, hydroxymethylene, alkanoyloxymethylene or aroyloxymethylene of up to 10 carbon atoms in the alkanoyl or aroyl or alkoxymethylene of up to 6 carbon atoms in the alkoxy; U is chlorine or bromine; R 1 , r 2 , and R 3 are alkyl of 1-4 carbon atoms; and R 4 is alkyl of 1-10 carbon atoms; comprising the steps of: (a) reacting an octahydronaphthalene compound of the formula ##STR15## in the presence of a base, with a trialkyl chlorosilane of the formula (R.sub.5).sub.3 Si--Cl wherein R 5 is alkyl of 1-4 carbon atoms, to produce a hexahydronaphthalene compound of the formula ##STR16## (b) hydrogenating the thus-produced hexahydronaphthalene compound in an inert solvent with hydrogen in the presence of a platinum-, palladium-, or rhodium-containing hydrogenation catalyst, to an ocathydronaphthalene compound of the formula ##STR17## and (c) reacting a vinyl ketone of the formula XCOCH═CH.sub.2 with the thus-produced octahydronaphthalene compound in an inert solvent in the presence of a Lewis acid; wherein all three reaction steps are conducted in anhydrous, alcohol-free solvents.
Claim 2
Dependent Claim
222 words
A process for preparing a trans-decahydronaphthalene compound of the formula ##STR13## wherein X is alkyl of 1-4 carbon atoms, --(CH 2 ) 3 --Z--R 2 ##STR14## --(CH 2 ) 3 COOR 4 , or --(CH 2 ) 3 CN; Y and Z are alkylenedioxymethylene of up to 6 carbon atoms in the alkylene, hydroxymethylene, alkanoyloxymethylene or aroyloxymethylene of up to 10 carbon atoms in the alkanoyl or aroyl or alkoxymethylene of up to 6 carbon atoms in the alkoxy; U is chlorine or bromine; R 1 , r 2 , and R 3 are alkyl of 1-4 carbon atoms; and R 4 is alkyl of 1-10 carbon atoms; comprising the steps of: (a) reacting an octahydronaphthalene compound of the formula ##STR15## in the presence of a base, with a trialkyl chlorosilane of the formula (R.sub.5).sub.3 Si--Cl wherein R 5 is alkyl of 1-4 carbon atoms, to produce a hexahydronaphthalene compound of the formula ##STR16## (b) hydrogenating the thus-produced hexahydronaphthalene compound in an inert solvent with hydrogen in the presence of a platinum-, palladium-, or rhodium-containing hydrogenation catalyst, to an ocathydronaphthalene compound of the formula ##STR17## and (c) reacting a vinyl ketone of the formula XCOCH═CH.sub.2 with the thus-produced octahydronaphthalene compound in an inert solvent in the presence of a Lewis acid; wherein all three reaction steps are conducted in anhydrous, alcohol-free solvents.
Claim 3
Dependent Claim
13 words
The process of claim 1, wherein X is alkyl of 1-4 carbon atoms.
Claim 4
Dependent Claim
15 words
The process of claim 1, wherein X is --(CH 2 ) 3 --Z--R 2 .
Claim 5
Dependent Claim
29 words
The process of claim 3, wherein Z is alkylenedioxymethylene and alkylene is of up to 6 carbon atoms with 2-3 carbon atoms in the chain linking the oxygen atoms.
Claim 6
Dependent Claim
9 words
The process of claim 3, herein Z is o-phenylenedioxymethylene.
Claim 7
Dependent Claim
9 words
The process of claim 3, wherein Z is hydroxymethylene.
Claim 8
Dependent Claim
23 words
The process of claim 3, wherein Z is alkanoyl or aroyloxymethylene and alkanoyl and aroyl each are of up to 10 carbon atoms.
Claim 9
Dependent Claim
18 words
The process of claim 3, wherein Z is alkoxymethylene and alkoxy is of up to 6 carbon atoms.
Claim 10
Dependent Claim
15 words
The process of claim 1, wherein X is ##STR18## and U is chlorine or bromine.
Claim 11
Dependent Claim
15 words
The process of claim 1, wherein X is --(CH 2 ) 3 COOR 4 .
Claim 12
Dependent Claim
13 words
The process of claim 1, wherein X is --(CH 2 ) 3 CN.
Claim 13
Dependent Claim
29 words
The process of claim 1, wherein Y is alkylenedioxymethylene and alkylene is of up to 6 carbon atoms with 2-3 carbon atoms in the chain linking the oxygen atoms.
Claim 14
Dependent Claim
9 words
The process of claim 1, wherein Y is hydroxymethylene.
Claim 15
Dependent Claim
23 words
The process of claim 1, wherein Y is alkanoyl- or aroyloxymethylene and alkanoyl or aroyl are each of up to 10 carbon atoms.
Claim 16
Dependent Claim
18 words
The process of claim 1, wherein Y is alkoxymethylene and alkoxy is of up to 6 carbon atoms.
Claim 17
Dependent Claim
9 words
The process of claim 1, wherein Y is o-phenylenedioxymethylene.
Claim 18
Dependent Claim
21 words
The process of claim 1, wherein the octahydronaphthalene compound is converted to an enolate prior to reaction with the trialkyl chlorosilane.
Claim 19
Dependent Claim
19 words
The process of claim 1, wherein the octahydronaphthalene compound is reacted with the trialkyl chlorosilane in a tertiary amine.
Claim 20
Dependent Claim
12 words
The process of claim 1, wherein the Lewis acid is titanium tetrachloride.
Claim 21
Dependent Claim
12 words
The process of claim 1, wherein the Lewis acid is tin(IV) chloride.
References Cited (Backward Citations)
US3816536A
Cited
US3839453A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-03-06 | 1981-09-05 | 1982-03-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-03-06 | 1985-09-05 | 1986-03-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-03-06 | 1989-09-05 | 1990-03-07 | $7700.00 | Window Closed / Lapsed |