Process for the preparation of trans-deca hydronaphthalene derivatives

US4077996A · kind A · utility

Assignee

• SCHERING CORPORATION · US

Inventors

• Gerhard Sauer · Berlin, DE
• Ulrich Eder · Berlin, DE
• Gregor Haffer · Berlin, DE
• Gunter Neef · Berlin, DE
• Rudolf Wiechert · Berlin, DE

Key dates

• Filing date: Apr 14, 1976
• Grant date: Mar 7, 1978
• Expiry date: Apr 14, 1996

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F7/1804
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for the preparation of trans-decahydronaphthalene compounds of Formula I ##STR1## wherein X is lower alkyl, --(CH.sub.2).sub.3 --Z--R.sub.2, ##STR2## --(CH.sub.2).sub.3 COOR.sub.4, or --(CH.sub.2).sub.3 CN; Y and Z are ketalized carbonyl or free, esterified, or etherified hydroxymethylene; PA1 U is halogen; PA1 R.sub.1, r.sub.2, and R.sub.3 are lower alkyl; and PA1 R.sub.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 EQU (R.sub.5).sub.3 Si--Cl wherein the R.sub.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 EQU XCOCH.dbd.CH.sub.2 is added to the thus-obtained octahydronaphthalene compound in an inert solvent in the presence of a Lewis acid.