PROCESS FOR THE PREPARATION OF 13-CIS-RETINOIC ACID

A process for the preparation of 13-cis-retinoic acid (I) (see formula I) from 3-methyl-5-(2,6,6-trimethyl-1-cyclohexan-1-yl)-2,4-pentadienyl)-triphenylphosphonium chloride (IIa) (see formula IIa) and 5-hydroxy-4-methyl-2(5H)-furanone (III) (see formula III) is herein disclosed. Compounds (IIa) and...

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Hauptverfasser:	ASPARI, PATRIZIO, BRAGLIA, RICCARDO, BRAGLIA, ENRICO, MOSSI, WALDO
Format:	Patent
Sprache:	eng ; fre
Schlagworte:	ACYCLIC OR CARBOCYCLIC COMPOUNDS CHEMISTRY HUMAN NECESSITIES HYGIENE MEDICAL OR VETERINARY SCIENCE METALLURGY ORGANIC CHEMISTRY PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
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Beschreibung
Zusammenfassung:	A process for the preparation of 13-cis-retinoic acid (I) (see formula I) from 3-methyl-5-(2,6,6-trimethyl-1-cyclohexan-1-yl)-2,4-pentadienyl)-triphenylphosphonium chloride (IIa) (see formula IIa) and 5-hydroxy-4-methyl-2(5H)-furanone (III) (see formula III) is herein disclosed. Compounds (IIa) and (III) are reacted in ethanol as the solvent and KOH as the base at a temperature ranging from -5 to 0°C to give a mixture of retinoic acids which is isomerised to (I) by treatment with a palladium complex. Divulgation d'un procédé de préparation d'acide 13-cis-rétinoïque (I) (voir la formule I) à partir de chlorure de (3-méthyl-5-(2,6,6-triméthylcyclohexan-1-yl)penta-2,4-diényl)- triphénylphosphonium (IIa) (voir la formule IIa) et de 5-hydroxy-4-méthyl-(5H)-furane -2-one (III) (voir la formule III). Les composés IIa et III réagissent dans de l'éthanol (solvant) et du KOH (base) à une température allant de -5 à 0 degré C pour donner un mélange d'acides rétinoïques qui est isomérisé en (I) au moyen d'un traitement avec un complexe de palladium.