Optically active ketals, processes for their preparation and...

C - Chemistry – Metallurgy – 07 – D

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260/351.1, 260/3

C07D 317/32 (2006.01) C07C 45/46 (2006.01) C07C 49/807 (2006.01) C07C 51/00 (2006.01) C07D 403/06 (2006.01) C07D 409/04 (2006.01)

Patent

CA 1281029

ABSTRACT OF THE DISCLOSURE Compounds of formula Image (I) wherein Ar is selected from the group consisting of phenyl, diphenyl, naphthyl, thienyl and pyrrolyl which groups may be substituted by a substituent selected from the group consisting of halogen atoms, C1-C4-alkyl, C3-C6-cycloalkyl, benzyl, hydroxy, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl, C1-C4-haloalkoxy, phenoxy, thienylcarbonyl and benzoyl, R repreents a C1-C4 alkyl; R1 and R2, which may be the same or different, represent a hydroxy, an O-M+, an OR3 or an Image group, R3 represents a C1-C24 alkyl, a C3-C6 cycloalkyl, a phenyl or a benzyl group; M+ represents the cation of an alkaline metal; R4 and R5, equal to or different from each other, represent a hydrogen atom, a C1-C4 alkyl, a C5-C6 cycloalkyl, a (CH2)n-CH2OH group with n=1, 2 or 3, or R4 and R5 together form a group (CH2)m with m=4 or 5; a group -CH2-CH2-R6-CH2-CH2- in which R6 is an oxygen atom, an N-H or N- (C1-C4) alkyl group; X represents a hydroxy, aacetoxy, trifluoro- acetoxy, trichloroacetoxy, benzoyloxy, 4-nitrobenzoyloxy, mesyloxy, benzensulphonyloxy or tosyloxy group, the carbon atoms marked by an asterisk being both contemporaneously in the R or S configuration. The preparation of the compound of formula I by ketalization or by trans-ketalization with tartaric acid derivatives and their rearrangement into alpha-arylalkanoic acids is described too.

478586

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