Process for preparing racemic...

Details Process for preparing racemic... Process for preparing racemic...

2006-07-03

2009-06-23

Puttlitz, Karl J (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C562S598000, C562S602000

Reexamination Certificate

active

07550626

ABSTRACT:
A process for preparing racemic alkyl-5-halopent-4-enecarboxylic acids and esters thereof of the formula (I), in which R is a C1-C6-alkyl radical, R1is H or C1-4-alkyl and X is chlorine, bromine or iodine, which comprises a) reacting a dialkyl alkylmalonate of the formula (II),in which R is as defined above and R2is a C1-C4-alkyl radical, in the presence of a metal alkoxide of the formula MOR3, in which M may be Na, K or Li, and R3is a C1-C4-alkyl radical, and in an organic solvent, with 1,3-dihalopropene to give the corresponding allylated malonate, then b) after full conversion, adding an inorganic salt and a C1-C6alcohol to the reaction mixture, heating the reaction mixture to reflux temperature, then c) isolating the desired racemic ester of the formula (I) from the reaction mixture by extraction or direct distillation and d) if the racemic acid is the desired end product, hydrolyzing the ester function.

REFERENCES:
patent: 7232925 (2007-06-01), Mori et al.
patent: 2007/0191630 (2007-08-01), Sakaeda et al.
patent: 2004/052828 (2005-09-01), None
patent: 2006/041062 (2006-04-01), None
International Search Report for PCT/EP2006/006438 mailed Oct. 10, 2006.
Izv. Akad. Nauk Armyan SSR 1960, 13, 259, Chemical Abstract 1961, 55, 20950h.

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