Process For Making Epoxide Derivatives of Farnesene and Use Thereof in Further Synthesis
AssigneeGivaudan SA
InventorsGiacomo PERSIANI, Corinne BAUMGARTNER, Thierry GRANIER, Martin LOVCHIK, Fridtjof SCHROEDER
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Abstract
Described herein are methods for making intermediates in the production of fragrance ingredients starting from β-farnesene. In particular, methods for making acetylmethylfarnesol and hydroxy-farnesylacetone are described. Methods for making other intermediates in the process are also described. In addition, compositions comprising intermediates in the process and uses of the intermediates are described.
Claims19
A method for making a compound of Formula (I), a compound of Formula (II) or a mixture thereof,
- wherein the method comprises contacting a compound of Formula (III) with a catalyst comprising a metal complexed with a salen ligand or a porphyrin ligand, wherein the salen ligand has Formula (IV) and wherein the porphyrin ligand has Formula (XI),
- wherein
- each ring A is independently selected from phenyl or naphthyl;
- each R1 is independently hydrogen, an alkyl group, an aryl group, or both R1 together with the carbon atoms to which R1 are attached form a cycloalkylene group, an arylene group, two or more cycloalkylene groups connected by a single bond or an alkyl group, two or more arylene groups connected by a single bond or an alkyl group, or a cycloalkylene and an arylene group connected by a single bond or an alkyl group;
- each R2 is independently hydrogen or an alkyl group;
- R3 is independently an alkyl group, an alkoxy group, an alkaryl group, an alkylsilyl ether group, or a halide;
- R4 is independently an alkyl group, an alkoxy group, an alkaryl group, an alkylsilyl ether group, or a halide;
- R9 is selected from hydrogen, an optionally substituted alkyl group, an optionally substituted aryl group, hydroxyl or an amino group;
- each n is selected from 0 to 4;
- m is selected from 0 to 4;
- each R6 is independently selected from hydrogen, an optionally substituted alkyl group, an optionally substituted alkylidene group, an optionally substituted aryl group, or an optionally substituted heteroaromatic group;
- and
- each R7 is independently selected from hydrogen, an alkyl group, an ester-containing alkyl group or a carboxylic acid containing alkyl group.
A method for making a compound of Formula (V), a compound of Formula (VI) or a mixture thereof,
- wherein the method comprises contacting a compound of Formula (I), a compound of Formula (II) or a mixture thereof with a compound of Formula (VII) and a palladium catalyst
- wherein R is selected from the group consisting of hydrogen and a C1 to C6 alkyl group;
- and R′ is selected from the group consisting of a C1 to C6 alkyl group and an OR group.
A method for making a compound of Formula (VIII), a compound of Formula (IX) or a mixture thereof,
- wherein the method comprises hydrolysis and decarboxylation of a compound of Formula (V), a compound of Formula (VI), or a mixture thereof,
- wherein R′ is selected from the group consisting of a C1 to C6 alkyl group and an OR group, and wherein R is selected from the group consisting of hydrogen or a C1 to C6 alkyl group.
A method for making a compound of Formula (VIII), a compound of Formula (IX) or a mixture thereof, wherein R′ is methyl,
- wherein the method comprises contacting a compound of Formula (I), a compound of Formula (II) or a mixture thereof with acetone and a palladium catalyst.
A method for making a compound of Formula (IX), a compound of Formula (VIII), or a mixture thereof, wherein R′ is methyl,
- the method comprising a palladium-catalysed Wacker oxidation of a compound of Formula (X), a compound of Formula (XII), or a mixture thereof.
A method for making a compound of Formula (X), a compound of Formula (XII), or a mixture thereof,
- wherein the method comprises a copper-catalysed alkylation of a compound of Formula (II), a compound of Formula (I), or a mixture thereof
(canceled)
A method of separation of a mixture of a compound of Formula (I) and a compound of Formula (II),
- wherein the method comprises the distillation of a mixture of a compound of Formula (I) and a compound of Formula (II).
A compound of Formula (V), a compound of Formula (VI) or a mixture thereof,
- wherein R is selected from the group consisting of hydrogen and a C1 to C6 alkyl group;
- and R′ is selected from the group consisting of a C1 to C6 alkyl group and an OR group.
A compound of Formula (X), a compound of Formula (XII), or a mixture thereof
(canceled)
(canceled)
(canceled)
Dependencies are inferred from the claim text.