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US 9,981,897 B2Granted
Ethers of bis(hydroxymethyl)cyclohexanes
AssigneeBASF SE
InventorsRalf Pelzer, Roland Merten, Pierre Fournier, Markus C. Biel
Life of this patent
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Abstract
The present invention relates to ethers of 1,2-, 1,3- and 1,4-bis(hydroxymethyl)cyclohexanes, to the preparation of such ethers and also to the use of such ethers as fragrances and as formulation auxiliaries in fragrance-comprising preparations.
Claims35
A cyclohexane derivative with a structure according to formula 1c
- wherein the substituents on the cyclohexyl ring may be in cis or trans position to one another, and
- R1 to R6 independently of one another are selected from the group consisting of C2-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C2-C6-alkenyl and hydrogen, and R1 and R2 are not hydrogen,
- with the proviso that the summed total number of the carbon atoms in all radicals R1 to R6 is only a whole numerical value up to 20.
A fragrance, flavor, or formulation auxiliary comprising a cyclohexane derivative with a structure according to formula 1c
- wherein the substituents on the cyclohexyl ring may be in cis or trans position to one another, and
- R1 to R6 independently of one another are selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C2-C6-alkenyl and hydrogen, and at least one radical from R1 and R2 is not hydrogen,
- with the proviso that the summed total number of the carbon atoms in all radicals R1 to R6 is only a whole numerical value up to 20.
A process for preparing a cyclohexane derivative with a structure according to formula 1c
- R1 and R2 independently of one another are selected from the group consisting of Rb and hydrogen,
- R3 to R6 independently of one another are selected from the group consisting of Ra and hydrogen,
- Ra is C1- to C6-alkyl, C3- to C6-cycloalkyl, C3- to C6-cycloalkenyl, or C2- to C6-alkenyl, and
- Rb is C1- to C6-alkyl, C3- to C6-cycloalkyl or C2- to C6-alkenyl,
- with the proviso that at least one radical from R1 and R2 is C2-C6-alkenyl;
- said process comprising
- reacting a cyclohexane derivative of the corresponding formula 2c
- with at least one C2-C6-alkyne to obtain the cyclohexane derivative of the formula 1c,
- wherein, in the cyclohexane derivative of the formula 2c,
- R3 to R6 independently of one another are selected from the group consisting of Ra and hydrogen,
- R11 and R12 are hydrogen or a group Rd, wherein at least one of the radicals, R11 and/or R12, is hydrogen,
- Ra is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl or C2-C6-alkenyl, and
- Rd is C1-C6-alkyl, C3-C6-cycloalkyl or C2-C6-alkenyl,
- wherein the radicals R11, R12, R3 to R6 and the C2-C6-alkyne are selected such that the summed total number of carbon atoms in all radicals R1 to R6 in the resultant compounds of the formula 1c, respectively, is a whole numerical value from 2 to 20,
- and wherein the cyclohexane derivative of the formula 1c is obtained,
- in which R1 is selected from C2-C6-alkenyl if R11 is hydrogen, and
- in which R2 is selected from C2-C6-alkenyl if R12 is hydrogen.
14 more elements
A process for preparing a cyclohexane derivative with a structure according to formula 1c
- R1 is selected from the group consisting of Rc and hydrogen,
- R2 is Rc,
- R3 to R6, independently of one another, are selected from the group consisting of Rc and hydrogen, and
- Rc is C1-C6-alkyl or C3-C6-cycloalkyl,
- with the proviso that at least one of the radicals, R1 and/or R2, is C2-C6-alkyl or C3-C6-cycloalkyl;
- said process comprising
- hydrogenating a cyclohexane derivative of the formula 3c
- with hydrogen to obtain the cyclohexane derivative of the formula 1c,
- wherein, in the further cyclohexane derivative of the formula 3c,
- R21 is selected from the group consisting of Ra and hydrogen,
- R22 is Ra,
- R23 to R26 independently of one another are selected from the group consisting of Ra and hydrogen,
- Ra is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl or C2-C6-alkenyl, and
- at least one of the radicals R21 to R26 is C3-C6-cycloalkenyl or C2-C6-alkenyl,
- wherein the radicals R21 to R26 are selected such that the summed total number of carbon atoms in all radicals R21 to R26 may only represent a whole numerical value from 2 to 20.
12 more elements
A process for preparing a cyclohexane derivative with a structure according to formula 1c,
- R1 is selected from the group consisting of hydrogen and Rc,
- R2 is selected from the group consisting of hydrogen and Rc,
- R3 to R6 independently of one another are selected from the group consisting of Rc and hydrogen
- Rc is C1-C6-alkyl or C3-C6-cycloalkyl,
- with the proviso that at least one of R1 and R2 is C2-C6-alkyl,
- said process comprising:
- reacting a cyclohexane derivative of the corresponding formula 2c
- with at least one C2-C6-alkyne,
- wherein, in the second cyclohexane derivatives of the formula 2c,
- R3 to R6 independently of one another are selected from the group consisting of Rf and hydrogen,
- R11 and R12 are hydrogen or a group Re, wherein at least one of the radicals R11 and/or R12 is hydrogen,
- Re and Rf are C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl or C3-C6-cycloalkenyl,
- R11, R12, R3 to R6 and the C2-C6-alkyne are selected such that the summed total number of carbon atoms in all radicals R1 to R6 in the resultant compounds of the formula 1c represents a whole numerical value from 2 to 20,
- wherein a cyclohexane derivative of the formula 1cc is obtained,
- wherein
- R1 and R2 are hydrogen or a group Re,
- R1 is C2-C6-alkenyl if R11 is hydrogen,
- R2 is C2-C6-alkenyl if R12 is hydrogen,
- R3 to R6 independently of one another are selected from the group consisting of Rf and hydrogen,
- the summed total number of carbon atoms in all radicals R1, R2, R3, R4, R5 and R6 represents a whole numerical value from 2 to 20, and
- hydrogenating the cyclohexane derivative of the formula 1cc with hydrogen.
18 more elements
A process for preparing a cyclohexane derivative of the formula 1cc,
- wherein the substituents on the cyclohexyl ring may be in cis or trans position to one another, and
- R1 and R2 are hydrogen or a group Re, wherein at least one of R1 and R2 is C2-C6-alkenyl,
- R3 to R6 independently of one another are selected from the group consisting of Rf and hydrogen,
- Re and Rf are C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl or C3-C6-cycloalkenyl, and
- the summed total number of carbon atoms in all radicals R1, R2, R3, R4, R5 and R6 of the formula 1cc, respectively, represents a whole numerical value from 2 to 20,
- said process comprising:
- reacting a cyclohexane derivative of the corresponding formula 2c
- with at least one C2-C6-alkenyl donor compound in the presence of a transition metal catalyst or a base,
- wherein, in the cyclohexane derivative of the formula 2c,
- R3 to R6 independently of one another are selected from the group consisting of Rf and hydrogen,
- R11 and R12 are hydrogen or a group Re, wherein at least one of R11 and R12 is hydrogen,
- Re and Rf are C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl or C3-C6-cycloalkenyl,
- R11, R12, R3 to R6 and the alkyne are selected such that the summed total number of carbon atoms in all radicals R1 to R6 in the resultant compounds of the formula 1c represents a whole numerical value from 2 to 20,
- to give a cyclohexane derivative of the formula 1cc,
- wherein R1 is C2-C6-alkenyl if R11 is hydrogen, and R2 is C2-C6-alkenyl if R12 is hydrogen.
12 more elements
A process for preparing a cyclohexane derivative with a structure according to formula 1c,
- R1 is selected from the group consisting of hydrogen and Rc,
- R2 is selected from the group consisting of hydrogen and Rc,
- R3 to R6 independently of one another are selected from the group consisting of Rc and hydrogen,
- Rc is C1-C6-alkyl or C3-C6-cycloalkyl,
- with the proviso that at least one radical from R1 and R2 is C2-C6-alkyl;
- said process comprising
- reacting a cyclohexane derivative of the corresponding formula 2c
- with at least one C2-C6-alkenyl donor compound in the presence of a transition metal catalyst or a base,
- wherein, in the cyclohexane derivative of the formula 2c,
- R3 to R6 independently of one another are selected from the group consisting of Rf and hydrogen,
- R11 and R12 are hydrogen or a group Re, wherein at least one of R11 and R12 is hydrogen,
- Re and Rf are C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl or C3-C6-cycloalkenyl,
- R11, R12, R3 to R6 and the alkyne are selected such that the summed total number of carbon atoms in all radicals R1 to R6 in the resultant compounds of the formula 1c represents a whole numerical value from 2 to 20,
- to give a cyclohexane derivative of the formula 1cc
- wherein R1 is C2-C6-alkenyl if R11 is hydrogen, and R2 is C2-C6-alkenyl if R12 is hydrogen, and
- hydrogenating the cyclohexane derivative of the formula 1cc with hydrogen.
13 more elements
A method of imparting or modifying a scent or a flavor to a composition comprising incorporating a cyclohexane derivative into a composition in an amount that imparts or modifies the scent or the flavor of the composition, wherein the cyclohexane derivative has a structure according to formula 1c
- wherein the substituents on the cyclohexyl ring may be in cis or trans position to one another, and
- R3 to R6 are hydrogen, and R1 and R2 independently of one another are selected from the group consisting of C2-C6-alkyl, C5-alkenyl, C3-C6-cycloalkenyl and C3-C6-cycloalkyl, or
- at least one radical from R3 to R6 is not methyl or hydrogen, and the other radicals R3 to R6 independently of one another are selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C2-C6-alkenyl and hydrogen, and R1 and R2 independently of one another are selected from the group consisting of C1-C6-alkyl, C2-C5-alkenyl, C3-C6-cycloalkenyl and C3-C6-cycloalkyl, or
- at least one radical from R1 and R2 is not methyl or ethyl, R3 and R4 are methyl, R5 and R6 are hydrogen, and also R1 and R2 independently of one another are selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, and C2-C6-alkenyl, or
- R1 and R2 independently of one another are selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, and C2-C6-alkenyl, and at least one radical from R3 to R6 is not hydrogen, with the exception of compounds of the formula 1c in which R1 and R2 are methyl or ethyl and at the same time R3 and R4 are each methyl and R5 and R6 are each hydrogen,
- and if R1 is hydrogen, R2 is not methyl, C4-alkyl, or vinyl,
- with the proviso that the summed total number of the carbon atoms in all radicals R1 to R6 is only a whole numerical value from 2 to 20.
4 more elements
Dependencies are inferred from the claim text.