Preparation of muscone, intermediates for this preparation and preparation of said intermediates

US5081311A · kind A · utility

Assignee

• BASF SE

Inventors

• Michael Huellmann · Heppenheim, DE
• Thomas Kuekenhoehner · Bischofswerda, DE
• Karl Brenner · Ludwigshafen, DE
• Rainer Becker · Bad Dürkheim, DE
• Matthias Irgang · Heidelberg, DE
• Charles Schommer · Ludwigshafen, DE

Key dates

• Filing date: May 18, 1990
• Grant date: Jan 14, 1992
• Expiry date: May 18, 2010

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C45/72
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Muscone of the formula I ##STR1## is prepared by a process in which an open-chain 2,15-diketone of the general formula II EQU CH.sub.3 --CO--X--CO--CH.sub.3 (II) where X is one of the radicals EQU --(--CH.sub.2 --).sub.12 -- (a) EQU --CH.dbd.CH--(--CH.sub.2 --).sub.8 --CH.dbd.CH-- (b) EQU --CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.6 --CH.dbd.CH--CH.sub.2 --(c) EQU --CH.sub.2 --CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.4 --CH.dbd.CH--CH.sub.2 --CH.sub.2 -- (d) or EQU --CH.sub.2 --CH.sub.2 CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.2 --CH.dbd.CH--CH.sub.2 --CH.sub.2 --CH.sub.2 -- (e) is brought into contact, at from 300.degree. to 400.degree. C. in the presence of from 5 to 15% by weight, based on the amount of catalyst, of water, in the gas phase, with a fixed-bed catalyst containing TiO.sub.2, CeO.sub.2 or the ThO.sub.2 as the catalytically active compound and the unsaturated cyclic ketone formed by intramolecular aldol condensation is subjected to catalytic hydrogenation. Furthermore, the open-chain unsaturated ketones of the formulae IIb, IIc and IId and advantageous processes for their preparation and their use as intermediates for a simple industrial synthesis of muscone are cl…