Process for the condensation of a carbonyl compound with an aromatic derivative in a basic medium
AssigneeRhodia Chimie, France
InventorsRoland Jacquot, Michel Spagnol
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Abstract
The invention concerns a condensation method for at least a carbonyl compound bearing at least an electroattractive group on an aromatic derivative bearing at least a hydroxyl function, characterised in that the electroattractive group present on the carbonyl compound is selected among fluoroalkyl derivatives, esters including orthoesters and nitriles and said condensation is carried out in a basic medium.
Claims39
A process for condensing at least one carbonyl compound carrying at least one electron-withdrawing group with an aromatic derivative carrying at least one hydroxyl functional group, wherein the electron-withdrawing group present on the carbonyl compound is selected from fluoroalkyl derivatives, esters, including orthoesters, and nitriles and said condensation is carried out in a basic medium.
The compound, characterized in that it is of formula II:
- 7
- in which:
- X4 is a nitrogen atom or C(R2) and
- R′1, R′2, R′3, R′4 and R′5, which are identical or different, are a hydrogen or halogen atom or a group selected from:
- C1 to C10 alkyls, these being linear or branched, C1 to C10 alkoxys, C1 to C10 alkyl ethers, amino, mono- or dialkylaminos, or C3 to C9 cycloalkyls or heterocycloalkyls, themselves optionally substituted by a halogen atom or a hydroxyl, amino or mono- or dialkylamino group,
- or either R′1 and R′2 or R′2 and R′3 constitute, with the bond established between them, an aromatic or heteroaromatic ring,
- with at least two of the R′1, R′3 and R′5 substituents being a group of formula III:
- 8
- in which
- the X units, which are identical or different, are a hydrogen atom, a halogen atom, preferably fluorine, or a radical of formula CnX2n+1 with n being an integer at most equal to 5, preferably to 2;
- p is an integer at most equal to 2;
- the X′ unit is a hydrogen atom or a group selected from C5 to C18 aryls, linear or branched C1 to C13 alkyls or linear or branched C2 to C14 alkenyls, if appropriate substituted. The substituents can in particular be a hydroxyl group, a halogen atom, a C1-C11 alkyl group and/or a amino group;
- with the possibility that the X′ unit be bonded to one CX2 to form a C4 to C8 ring;
- the symbol EWG is an electron-withdrawing group advantageously a fluorine atom or a perfluorinated residue of formula Cn′X2n′+1 with n′ being a integer at most equal to 8, with the proviso that at least one of the X or EWG units present on the carbon α to the hydroxy functional group is a fluorine atom, and with the total number of carbon atoms of the polyfluoroalkyl derivative of formula III between 1 and 15, preferably between 1 and 10.
Dependencies are inferred from the claim text.