Process for preparing 2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane

US10875873B2 · kind B2 · utility

Assignee

• BASF AGRO B.V. · NL

Inventors

• Stefan Benson · Bensheim, DE
• Michael Rack · Eppelheim, DE
• Roland Goetz · Ludwigshafen, DE
• Bernd Wolf · Niederkirchen, DE
• Joachim Gebhardt · Monsheim, DE
• Helmut Kraus · Cologne, DE

Key dates

• Filing date: Feb 5, 2018
• Grant date: Dec 29, 2020
• Expiry date: Feb 5, 2038

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D493/08
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-iso-propyl-7-oxabicyclo[2.2.1]heptane of the formula (I), (I) any one of its individual enantiomers or any non-racemic mixture thereof comprising the steps of (a) deprotonating (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II), (II) any one of its individual enantiomers or any non-racemic mixture thereof in the presence of at least one base of the formula [Mm+]n [An-]m (III) wherein Mm+ represents a m-valent metal cation wherein m is an integer of 1 or 2, and An_ represents a n-valent anion wherein n is an integer of 1 or 2, said base being capable of forming a solvent S1 selected from water, a C1-C4 alkyl alcohol or any combination thereof under the reaction conditions, to form a metal alkoxide or metal alkoxide solvate of the formula (IV), (IV) any one of its individual enantiomers or any non-racemic mixture thereof wherein Mm+, m and the solvent S1 have the same meaning as defined for the base of formula (III), and x denotes a number from 0 to 10, and (b) reacting the metal alkoxide or metal alkoxide solvate of the formula (IV), any of its individual ena…