Process for the preparation of pure enatiomers of 4-[4-(4'-tert.butylphenyl)-2-hydroxybutoxy]-benzoic acid and its alkyl ester

The pure enantiomers of LIFIBROL and its alkyl esters can be prepared in surprisingly good yields by reacting the pure enantiomeric forms of S(-)- or R(+)-4-(4'-tert.butylphenyl)-1,2-epoxybutane with alkyl 4-hydroxybenzoate in DMF at increased temperature and in the presence of the sodium salt...

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Hauptverfasser: HENSCHEL, HANS-HELMUT, REITER, FRIEDEMANN
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creator HENSCHEL, HANS-HELMUT
REITER, FRIEDEMANN
description The pure enantiomers of LIFIBROL and its alkyl esters can be prepared in surprisingly good yields by reacting the pure enantiomeric forms of S(-)- or R(+)-4-(4'-tert.butylphenyl)-1,2-epoxybutane with alkyl 4-hydroxybenzoate in DMF at increased temperature and in the presence of the sodium salt of alkyl 4-hydroxybenzoate. The crude reaction product is subsequently to be separated off. Either the stereochemically pure LIFIBROL ester is obtained by recrystallisation, or the precipitated LIFIBROL enantiomer is prepared in pure crystalline form by mild alkaline hydrolysis followed by acidification.
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subjects ACYCLIC OR CARBOCYCLIC COMPOUNDS
APPARATUS THEREFOR
CHEMISTRY
GENERAL METHODS OF ORGANIC CHEMISTRY
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
title Process for the preparation of pure enatiomers of 4-[4-(4'-tert.butylphenyl)-2-hydroxybutoxy]-benzoic acid and its alkyl ester
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