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US 2024/0368068 A1Published application
Process for preparing perfuming intermediates
AssigneeFirmenich SA
InventorsOliver KNOPFF, Nicolas POIRIER
Life of this patent
Estimating the term…
Abstract
The present invention relates to the field of perfumery. More particularly, it concerns valuable new chemical intermediates for producing perfuming ingredients. Moreover, the present invention comprises also a process for producing compound of formula (I).
Claims15
A process for the preparation of a compound of formula (I)
- in the form of any one of its stereoisomers or a mixture thereof, and wherein m is 0 or 1;
- Ra is a C1-4 alkyl group, a trimethyl silyl group, a C(═O)—Rc group, a C(═O)—ORc group, a CH2(ORc) group, a CH(ORc)CH3 group wherein Rc is a C1-4 alkyl group;
- Rb is a C1-4 alkyl group, a C(═O)—Rc group wherein Rc is a C1-4 alkyl group;
- or Ra and Rb are taken together and represent a C2-6 alkanediyl group and X is a group of formula a), b) or c);
- in the form of any one of its stereoisomers, and wherein each R1, R2, R3, R4, R5, R6 and R7, independently from each other, represent a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group, each optionally substituted by a hydroxy or C1-3 alkoxy group;
- or two groups among R1, R2, R3, R4, R5, R6 and R7 are taken together and form C3-8 cycloalkyl or C5-8 cycloalkenyl group, each optionally substituted by a hydroxy, C1-3 alkyl or C1-3 alkoxy group, and the others groups have the same meaning as defined above;
- each R8, R9 and R10, independently from each other, represent a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group, each optionally substituted by a hydroxy or C1-3 alkoxy group;
- or two groups among R8, R9 and R10 are taken together and form C3-8 cycloalkyl or C5-8 cycloalkenyl group, each optionally substituted by a hydroxy, C1-3 alkyl or C1-3 alkoxy group, and the other group has the same meaning as defined above;
- n is 0 or 1 and Y is a —CH═CR11—, —CHR12—CHR11— or —CH2—C(OH)R11— group wherein R11 is a hydrogen atom or a methyl or ethyl group and R12 is a hydroxy or a acetate group;
- provided that m is 1 when X is a group of formula b);
- comprising a cross metathesis step, in the presence of a metathesis catalyst, between compound of the formula (IIa), (IIb) or (IIc):
- in the form of any one of its stereoisomers, and wherein each R, R2, R3, R4, R5, R6, R7, R8, R9, R10, n and Y have the same meaning as defined above
- with compound of formula (III);
- in the form of any one of its stereoisomers or a mixture thereof, and wherein m is 0 or 1 when the cross metathesis step is performed with compound of the formula (IIa) or (IIc) or m is 1 when the cross metathesis step is performed with compound of the formula (IIb), Ra is a C1-4 alkyl group, a trimethyl silyl group, a C(═O)—Rc group, a C(═O)—ORc group, a CH2(ORc) group, a CH(ORc)CH3 group wherein Rc is a C1-4 alkyl group;
- Rb is a C1-4 alkyl group, a C(═O)—Rc group wherein Rc is a C1-4 alkyl group;
- or Ra and Rb are taken together and represent a C2-6 alkanediyl group, Rd is a hydrogen atom or a CH(ORa)(ORb)m group wherein m, Ra and Rb have the same meaning as defined above.
13 more elements
The process according to claim 11, wherein R2 is a hydrogen atom, a C1-3 alkyl group or a C2-3 alkenyl group.
A compound of formula (VIII):
- in the form of any one of its stereoisomers or a mixture thereof, and wherein X is a group of formula b) or d)
- in the form of any one of its stereoisomers, and
- wherein p is 0 when the dotted line is a carbon-carbon double bond and p is 1 when the dotted line is a carbon-carbon single bond;
- each R1, R2, R3, R4, R5, R6 and R7, independently from each other, represent a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group, each optionally substituted by a hydroxy or C1-3 alkoxy group;
- or two groups among R1, R2, R3, R4, R5, R6 and R7 are taken together and form C3-8 cycloalkyl or C5-8 cycloalkenyl group, each optionally substituted by a hydroxy, C1-3 alkyl or C1-3 alkoxy group, and the others groups have the same meaning as defined above;
- each R8, R9 and R10, independently from each other, represent a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group, each optionally substituted by a hydroxy or C1-3 alkoxy group;
- or two groups among R8, R9 and R10 are taken together and form C3-8 cycloalkyl or C5-8 cycloalkenyl group, each optionally substituted by a hydroxy, C1-3 alkyl or C1-3 alkoxy group, and the other group has the same meaning as defined above;
- n is 0 or 1;
- Y is a —CH═CR11—, —CHR12—CHR11— or —CH2—C(OH)R11— group wherein R11 is a hydrogen atom or a methyl or ethyl group and R12 is a hydroxy or a acetate group;
- Z is, when X is of formula d), a CHO group, a CH2OH group or a CH(ORa)(ORb)m group wherein m is 0 or 1, Ra is a C1-4 alkyl group, a trimethyl silyl group, a C(═O)—Rc group, a C(═O)—ORc group, a CH2(ORc) group, a CH(ORc)CH3 group wherein Rc is a C1-4 alkyl group;
- Rb is a C1-4 alkyl group, a C(═O)—Rc group wherein Rc is a C1-4 alkyl group;
- or Ra and Rb are taken together and represent a C2-6 alkanediyl group;
- or
- Z is, when X is of formula b), a CH(ORa)(ORb) group wherein Ra and Rb, independently from each other, are a methyl group or a C3-4 alkyl group, a C(═O)—Rc group wherein Rc is a C1-4 alkyl group;
- or Ra and Rb are taken together and represent a C3-6 alkanediyl group;
- and
- provided that when X is a group of formula (d), then at least one group among R1, R2, R3, R4, R5, R6 and R7 is a C1-6 alkyl group or a C2-6 alkenyl group, each optionally substituted by a hydroxy or C1-3 alkoxy group;
- provided that when X is a group of formula (d) and six groups among R1, R2, R3, R4, R5, R6 and R7 are a hydrogen atom, then the group among R1, R2, R3, R4, R5, R6 and R7 being not a hydrogen atom is not a methyl group;
- provided that when X is a group of formula (d) and R2, R3, R4, R5, R6 and R7 are a hydrogen atom then R1 is not a prop-1-en-2-yl group;
- and provided that 3-(4-(tert-butyl)cyclohex-1-en-1-yl)acrylaldehyde, 3-(4-(tert-butyl)-1-hydroxycyclohexyl)acrylaldehyde, 1-(tert-butyl)-4-(3,3-diethoxyprop-1-en-1-yl)benzene, 2-(4-(tert-butyl)styryl)-1,3-dioxolane, 3-(4-(tert-butyl)-1-hydroxycyclohexyl)allyl acetate, 3-(2-allyl-1-hydroxycyclohexyl)allyl acetate, 4-(tert-butyl)-1-(3-hydroxyprop-1-en-1-yl)cyclohexan-1-ol, 2-allyl-1-(3-hydroxyprop-1-en-1-yl)cyclohexan-1-ol, 2-(4-isopropylstyryl)-1,3-dioxane, 2-(4-isopropylstyryl)-4-methyl-1,3-dioxolane, 3-(2-(buta-1,3-dien-1-yl)-1-hydroxycyclohexyl)acrylaldehyde, 3-(5,5-dimethylcyclohex-1-en-1-yl)acrylaldehyde, 3-((1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-3-yl)acrylaldehyde, (1R,2S,5R)-1-(3-(tert-butoxy)prop-1-en-1-yl)-2-isopropyl-5-methylcyclohexan-1-ol, 2-allyl-1-(3-hydroxyprop-1-en-1-yl)cyclohexan-1-ol, (3,3-dimethoxyprop-1-en-1-yl)benzene, are excluded.
17 more elements
Dependencies are inferred from the claim text.