Stereoselective process for preparing (cyclo)alkyl...

Details Stereoselective process for preparing (cyclo)alkyl... Stereoselective process for preparing (cyclo)alkyl...

C - Chemistry, Metallurgy

07

C

C07C 51/353 (2006.01) C07C 59/54 (2006.01) C07D 317/34 (2006.01)

Patent

CA 2349209

A process for preparing an alkyl phenylglycolic acid is disclosed. It follows the sequence of condensing a substituted acetaldehyde with mandelic acid to provide a 5-phenyl-1,3-dioxolan-4-one, which is condensed with an alkyl ketone or aldehyde to provide a 5-(1-hydroxyalkyl)-5-phenyl-1,3-dioxolan-4-one, which is dehydrated to a 5-(1-alkenyl)-5-phenyl-1,3-dioxolan-4-one. The 5-(1- alkenyl)-5-phenyl-1,3-dioxolan-4-one may be hydrolyzed and reduced to an .alpha.-alkylphenylglycolic acid or the hydrolysis and reduction steps may be reversed. The process enables the production of single enantiomers of cyclohexylphenylglycolic acid (CHPGA). An analogous process for racemic CHPGA is disclosed employing racemic mandelic acid and acetone. Novel intermediates in the process are also disclosed.

L'invention concerne un procédé permettant de préparer un acide alkylphénylglycolique. Ce procédé se déroule comme suit: on condense un acétaldéhyde substitué avec de l'acide mandélique pour produire un 5-phényl-1,3-dioxolan-4-one, on condense ce dernier avec un alkyle cétone ou aldéhyde pour produire un 5-(1-hydroxyalkyl)-5-phényl-1,3-dioxolan-4-one, qu'on déshydrate pour obtenir un 5-(1-alcényl)-5-phényl-1,3-dioxolan-4-one. Ce 5-(1-alcényl)-5-phényl-1,3-dioxolan-4-one peut être hydrolysé et réduit pour former un acide .alpha.-alkylphénylglycolique, ou les étapes d'hydrolyse et de réduction peuvent être inversées. Ce procédé permet de produire des énantiomères distincts d'acide cyclohexylphénylglycolique (CHPGA). L'invention concerne également un procédé analogue permettant de produire du CHPGA racémique en utilisant un acide mandélique racémique et de l'acétone. L'invention concerne en outre les nouveaux produits intermédiaires de ce procédé.

Affiliated with

Also associated with

Rating

Stereoselective process for preparing (cyclo)alkyl... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Stereoselective process for preparing (cyclo)alkyl..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Stereoselective process for preparing (cyclo)alkyl... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFCA-PAI-O-1778390