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

US5120880A · 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: Sep 10, 1991
• Grant date: Jun 9, 1992
• Expiry date: Sep 10, 2011

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 PA1 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 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 …