Preparation, intermediates for the preparation and the use of a mixture of dodecdienol isomers

US5599848A · kind A · utility

Assignee

• BASF SE

Inventors

• Ulrich Klein · Schifferstadt, DE
• Ulrich Neumann · Schifferstadt, DE
• Wolfgang Mackenroth · Bad Dürkheim, DE
• Guenter Renz · Freinsheim, DE
• Wolfgang Krieg · Weingarten, DE
• Christiane Mackenroth · Bad Dürkheim, DE
• Ernst Buschmann · Ludwigshafen, DE
• Jacobus J. DeKramer · Schifferstadt, DE
• Roland Milli · Ilvesheim, DE

Key dates

• Filing date: Aug 7, 1995
• Grant date: Feb 4, 1997
• Expiry date: Aug 7, 2015

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for preparing a mixture of 8E,10E-dodecadienol (Ia), 8E,10Z-dodecadienol (Ib), 8Z,10E-dodecadienol (Ic) and 8Z,10Z-dodecadienol (Id), EQU H.sub.3 C--CH.dbd.CH--CH.dbd.CH--(CH.sub.2).sub.6 --CH.sub.2 --OH PA1 (8E,10E=Ia) PA1 (8E,10Z=Ib) PA1 (8Z,10E=Ic) PA1 (8Z,10Z=Id) starting from 1,8-octanediol (II) which is converted with a halogenating agent into (III) EQU Hal-CH.sub.2 --(CH.sub.2).sub.6 --CH.sub.2 --OH (III) where (III) is subsequently reacted with (IV), EQU H.sub.2 C.dbd.CH--O--R (IV) to give (V) EQU Hal-CH.sub.2 --(CH.sub.2).sub.6 --CH.sub.2 --O--CH(CH.sub.3)--OR(V), (V) is converted in the presence of magnesium and crotonaldehyde into (VI) EQU H.sub.3 C--CH.dbd.CH--CH(OH)--(CH.sub.2).sub.8 --O--CH(CH.sub.3)--OR(VI) and the protective group R and the hydroxyl group are simultaneously eliminated from (VI) in the presence of acid, novel intermediates for this process, and methods for controlling the codling moth Cydia pomonella by interfering with mating using this mixture are described.