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US 11,952,335 B2Granted
Process for preparing 1-indanone compounds by intramolecular Friedel-Crafts reaction of alpha,alpha-dialkylmalonate derivatives
AssigneeFirmenich SA
InventorsJean-François Basset, Philippe Dupau, Iris Magpantay, Murielle Haldimann Sanchez
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Abstract
Described herein are valuable new chemical intermediates for producing perfuming ingredients, and a process for producing compound of formula (I).
Claims15
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 n is an integer between 0 and 2, each R1, independently from each other, represents a substituent of the aromatic ring and is a C1-6 alkyl group, a C2-6 alkenyl group or a C1-6 alkoxy group;
- R2 represents a C1-3 alkyl group;
- and R3 represents a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group;
- comprising the cyclisation of a compound of the formula (II)
- in the form of any one of its stereoisomers or a mixture thereof, and wherein n, R1, R2 and R3 have the same meaning as defined in formula (I);
- and
- A represents a C(O)OC(O)R4 group, a C(O)Cl group or a COOH group wherein R4 represents a C1-6 alkyl group substituted by one or more chlorine or fluorine atoms;
- in a presence of a Friedel-Crafts acylation reagent.
5 more elements
A compound of formula
- in the form of any one of its stereoisomers or a mixture thereof, and wherein n is an integer between 0 and 2, each R1, independently from each other, represents a substituent of the aromatic ring and is a C1-6 alkyl group, a C2-6 alkenyl group or a C1-6 alkoxy group;
- R2 represents a C1-3 alkyl group;
- and R3 represents a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group;
- provided that 5-methoxy-2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylic acid, methyl 2-ethyl-5-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate, methyl 2-ethyl-6-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate, ethyl 1-oxo-2-propyl-2,3-dihydro-1H-indene-2-carboxylate, methyl 2-ethyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate, methyl 2-isopropyl-1-oxo-2,3-dihydro-1H-indene-2-carboxyl ate, methyl 6-methoxy-1-oxo-2-propyl-2,3-dihydro-1H-indene-2-carboxylate, 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylic acid, methyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate, ethyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate, allyl 2-methyl-1-oxo-2, 3-dihydro-1H-indene-2-carboxylate, methyl 6-methoxy-2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate, tert-butyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate, methyl 4-methoxy-2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate, methyl 5,6-dimethoxy-2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate, methyl 6-isobutyl-2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate, ethyl 5-(tert-butyl)-2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate, ethyl 2,5,7-trimethyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate and tert-butyl 5-methoxy-2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate are excluded.
1 more element
A compound of formula
- in the form of any one of its stereoisomers or a mixture thereof, and wherein n is an integer between 0 and 2, each R1, independently from each other, represents a substituent of the aromatic ring and is a C1-6 alkyl group, a C2-6 alkenyl group or a C1-6 alkoxy group;
- R2 represents a C1-3 alkyl group;
- R3 represents a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group and A represents a C(O)Cl group;
- a C(O)OC(O)R5 group, and R5 represents a C1-6 alkyl group provided that ethyl 3-chloro-2-(4-m ethoxy-3-methylbenzyl)-2-methyl-3-oxopropanoate is excluded.
1 more element
Dependencies are inferred from the claim text.