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US 2023/0365523 A1Published application
Process for preparing 3-(cyclohex-1-en-1-yl)propanal derivatives
OwnerOliver KNOPFF, Philippe DUPAU +5inventors
InventorsOliver KNOPFF, Philippe DUPAU, Jean-Jacques RIEDHAUSER, Nicolas POIRIER, Dilver Peña FUENTES, Armin BÖRNER, Luigi MARINONI
Life of this patent
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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).
Claims20
A process for the preparation of a compound of formula
- in the form of any one of its stereoisomers or a mixture thereof, 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 and the other groups have the same meaning as defined above;
- comprising a hydroformylation and an elimination step starting from compound of formula (II)
- in the form of any one of its stereoisomers or a mixture thereof, and wherein R1, R2, R3, R4, R5, R6 and R7 have the same meaning as defined in formula (I) and X represents a C(O)R group or a Si(R′)3 group wherein R is a hydrogen atom, a C1-4 alkyl group, a C1-4 alkoxy group or a phenyl group, R′, independently from each other, are a C1-4 alkyl group.
1 more element
A compound of formula
- in the form of any one of its stereoisomers or a mixture thereof, and wherein X represents a C(O)R group or a Si(R′)3 group wherein R is a hydrogen atom, a C1-4 alkyl group, a C1-4 alkoxy group or a phenyl group, R′, independently from each other, are a C1-4 alkyl group;
- 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 and the others groups have the same meaning as defined above;
- provided that 1-(3-oxopropyl)cyclohexyl acetate is excluded.
1 more element
A compound of formula
- in the form of any one of its stereoisomers or a mixture thereof, and wherein X′ is a hydrogen atom, a C1-3 alkyl group, a C2-3 alkenyl group, a benzyl group or a C(O)R group or a Si(R′)3 group wherein R is a hydrogen atom, a C1-4 alkyl group, a C1-4 alkoxy group or a phenyl group, R′, independently from each other, are a C1-4 alkyl group;
- 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 and the others groups have the same meaning as defined above;
- Ra and Rb, independently from each other, represent a C1-4 alkyl group or Ra and Rb are taken together and represent a C2-6 alkanediyl group;
- provided that 1-(2-(1,3-dioxolan-2-yl)ethyl)-4-isobutyl-2-methylcyclohexan-1-ol, 1-(2-(1,3-dioxolan-2-yl)ethyl)-4-isopropyl-2-methylcyclohexan-1-ol, 1-(3,3-diethoxypropyl)cyclohexan-1-ol, 1-(2-(1,3-dioxolan-2-yl)ethyl)-4-(tert-butyl)-2-methylcyclohexan-1-ol, 1-(2-(1,3-dioxolan-2-yl)ethyl)-4-(tert-butyl)cyclohexan-1-ol and 1-(2-(1,3-dioxan-2-yl)ethyl)-4-(tert-butyl)cyclohexan-1-ol are excluded.
2 more elements
A compound of formula
- in the form of any one of its stereoisomers or a mixture thereof, and wherein;
- each R1 and R2, 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;
- Ra and R1, independently from each other, represent a C1-4 alkyl group or Ra and Rb are taken together and represent a C2-6 alkanediyl group
A compound of formula
- in the form of any one of its stereoisomers or a mixture thereof, and wherein the dotted line represents a double or a triple bond;
- X represents a C(O)R group or a Si(R′)3 group wherein R is a hydrogen atom, a C1-4 alkyl group, a C1-4 alkoxy group or a phenyl group, R′, independently from each other, are a C1-4 alkyl group;
- 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 and the others groups have the same meaning as defined above;
- provided that 1-vinylcyclohexyl acetate, 1-ethynylcyclohexyl acetate, 1-vinylcyclohexyl propionate, 4-methyl-1-vinylcyclohexyl acetate, 2-methyl-1-vinylcyclohexyl acetate, 1-ethynyl-2-methylcyclohexyl acetate, 2-ethyl-1-vinylcyclohexyl acetate, 2-isopropyl-1-vinylcyclohexyl acetate, 2-secbutyl-1-vinylcyclohexyl acetate, 2-isopropyl-5-methyl-1-vinylcyclohexyl acetate, 2-allyl-1-vinylcyclohexyl acetate, 4-tert-butyl-1-vinylcyclohexyl acetate, 1-vinyldecahydronaphthalen-1-yl acetate and 1-ethynyldecahydronaphthalen-1-yl acetate are excluded.
2 more elements
Dependencies are inferred from the claim text.