Basf Agro B.v.

Stefan Benson

Michael Rack

Roland Goetz

Bernd Wolf

Helmut Kraus

Joachim Gebhardt

Sukunath Narayanan

Chidambaram Rishinaradamangalam

Klaus Ditrich

Christiane Alznauer

Roland GÖTZ

Chidambaram Rishinaradaman Galam

This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I), any one of its individual enantiomers or any non-racemic mixture thereof any one of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II), any one of its individual enantiomers or any non-racemic mixture thereof (as defined in the description) with elemental sodium to form a sodium salt of the formula (III), any one of its individual enantiomers or any non-racemic mixture thereof (as defined in the description), and (b) reacting said sodium salt (III) with a 2-Methylbenzyl compound of the formula (IV) wherein X is a leaving group, wherein the steps (a) and (b) are conducted in the presence of at least one substantially anhydrous inert organic solvent.

Process for preparing 2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicy-clo[2.2.1]heptane

The present invention relates to a method for separating an optically active hydroxy cineole derivatives by lixiviation and crystallization and enantiomerically pure optically active hydroxy cineole derivatives of purity greater than 99.5% that have been prepared by this process. The present invention further relates to use of the desired enantiomer having enantiomeric excess of at least 99.5% ee as prepared according to the present invention, for the synthesis of enantiomerically pure 7-oxabicyclo[2.2.1]heptane derivatives.

Method for separating optically active hydroxy cineole derivatives

The present invention relates to a process for preparing optically active 1,4-cineole derivatives by enzymatic resolution and enantiomerically pure optically active 1,4-cineole derivatives of purity greater than 99.9% that have been prepared by this process. The present invention further relates to a process for preparing 7-oxabicyclo[2.2.1]heptane derivatives from the enantiomerically pure optically active 1,4-cineole derivatives.

Process for preparing an optically active cineole derivative

This invention relates to a process for preparing (&#xb1;)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-iso-propyl-7-oxabicyclo[2.2.1]heptane of the formula (I) any of its individual enantiomers or any non-racemic mixture thereof, comprising the step of reacting (&#xb1;)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II) any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (III) wherein X is a leaving group, in the presence of at least one base, at least one catalyst selected from rubidium salts, cesium salts and any combination thereof and at least one inert organic solvent S1.

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

This invention relates to a process for the epoxidation of a tetrasubstituted alkene such as terpinolene to the corresponding epoxide such as terpinolene epoxide by reacting the tetrasubstituted alkene with performic acid prepared in situ from formic acid and hydrogen peroxide in the presence of at least one buffering agent. Further, the invention relates to the use of an oxidizing agent comprising hydrogen peroxide and formic acid for the in-situ epoxidation of a tetrasubstituted alkene.

Process for the epoxidation of a tetrasubstituted alkene

This invention relates to a process for preparing (&#xb1;)-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 (&#xb1;)-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 M, 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 enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (V), (V) wherein X is a leaving group, wherein the steps (a) and (b) are conducted in the presence of at least one inert organic solvent S2 and comprise a further step of (c) simultaneously removing the solvent S1 from the reaction mixture. 

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

This invention relates to a process for preparing (&#xb1;)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I) any of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of  

This invention relates to a process for the epoxidation of a tetrasubstituted alkene such as terpinolene to the corresponding epoxide such as terpinolene epoxide by reacting the tetrasubstituted alkene with peracetic acid prepared in situ from acetic anhydride and hydrogen peroxide in the presence of at least one buffering agent. Further, the invention relates to the use of an oxidizing agent comprising hydrogen peroxide and acetic anhydride for the in-situ epoxidation of a tetrasubstituted alkene.

The present invention relates to a process for the preparation of limonene-4-ol by an epoxide ring opening isomerization of terpinolene epoxide.

Process for the preparation of limonene-4-ol

The present invention relates to a process for the preparation of terpinolene epoxide by epoxidation of terpinolene.

Process for the preparation of terpinolene epoxide

The present invention relates to a process for preparing a mixture of terpene alcohols comprising limonene-4-ol and terpinene-4-ol from terpinolene epoxide via an isomerization and/or hydrogenation reaction in the presence of a copper catalyst.

Process for preparing a mixture of terpene alcohols

The present invention relates to a process for preparing terpinene-4-ol from limonene-4-ol via a hydrogenation reaction in the presence of a nickel catalyst.

Growing community of inventors

Ludwigshafen, Germany

Stefan Benson