NOUVEAU PROCEDE DE PREPARATION D'HYDROXY-ACIDES GRAS INSATURES

Preparation of hydroxy-ester compound (I) comprises reacting a phosphonate compound with a lactol compound by Wittig-Horner reaction to give (I) and subjecting (I) under saponification reaction to obtain a hydroxy-acid. Preparation of hydroxy-ester compound (I) of formula HO-CH 2-(CH 2) n-CH=C(R1)-C...

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Bibliographic Details
Main Authors BRAYER JEAN LOUIS, FOLLEAS BENOIT, FRISON NATACHA
Format Patent
LanguageFrench
Published 20.03.2009
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
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Summary:Preparation of hydroxy-ester compound (I) comprises reacting a phosphonate compound with a lactol compound by Wittig-Horner reaction to give (I) and subjecting (I) under saponification reaction to obtain a hydroxy-acid. Preparation of hydroxy-ester compound (I) of formula HO-CH 2-(CH 2) n-CH=C(R1)-C(=O)(OR3) comprises reacting a phosphonate compound of formula P(=O)((R2O) 2)-CH(R1)-C(=O)(OR4) with a lactol compound of formula (II) by Wittig-Horner reaction to give (I) and subjecting (I) under saponification reaction to obtain a hydroxy-acid of formula HO-CH 2-(CH 2) n-CH=C(R1)-C(=O)(OH). R3 : H or 1-6C alkyl, preferably ethyl; R1 : H, F, Cl, Br, CF 3 or 1-6C alkyl (optionally substituted by halo); n : greater than 4, preferably >=6; either R2 : 1-6C alkyl, preferably ethyl or methyl; or R2OP : a cyclic ring; and R4 : 1-6C alkyl, preferably ethyl. Provided that when R1 is hydrogen, then the reaction is carried out by Doebner-knoevenagel reaction using a malonic acid derivative of formula R 3OOC-CH 2-COOR 3. An independent claim is included for (I) obtained by the process. [Image].
Bibliography:Application Number: FR20050010765