Preparation of aralkanoic acids and esters using mixed...

C - Chemistry – Metallurgy – 07 – C

Patent

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C07C 57/30 (2006.01) C07C 51/14 (2006.01) C07C 57/40 (2006.01) C07C 59/64 (2006.01) C07C 67/38 (2006.01) C07C 69/612 (2006.01) C07C 69/616 (2006.01) C07D 207/20 (2006.01) C07D 209/46 (2006.01) C07D 263/57 (2006.01) C07D 333/24 (2006.01)

Patent

CA 2222020

The activity of a palladium catalyst in the carboxylation of an aralkene with carbon monoxide and water or an alcohol in the absence of oxygen can be enhanced when it is used in conjunction with (A) a ligand mixture comprising compounds corresponding to the formulas R3ZY and R'3Z wherein each R and R' is independently selected from alkyl, aryl and substituted aryl groups; Y is a member of Group VIA of the Periodic Table; and Z is an element having a Pauling electronegativity of 1.9-2.5 or (B) a complex ligand providing all of the elements of said mixture. The invention has particular utility in carboxylating an aralkene such as 4-isobutylstyrene or 2-methoxy-6- vinylnaphthalene to ibuprofen or naproxen or their esters; and the preferred novel ligand is usually a 50/50 mixture of phosphine and phosphine oxide.

Il est possible d'accroître l'activité d'un catalyseur au palladium dans la carboxylation d'un aralcène avec du monoxyde de carbone et de l'eau ou un alcool en l'absence d'oxygène lorsque l'on utilise ce catalyseur conjointement avec (A) un mélange de ligands comportant des composés correspondant aux formules R¿3?ZY et R'¿3?Z dans lesquelles chaque R et R' est choisi, de manière indépendante, dans des groupes alkyle, aryle et aryl à substitution et dans lesquelles Y représente un élément appartenant au groupe VIA du tableau de la classification périodique des éléments, Z représente un élément dont l'électronégativité de Pauling est comprise entre 1,9 et 2,5 ou, (B) un ligand complexe offrant tous les éléments dudit mélange. Cette invention se révèle particulièrement utile lors de la carboxylation d'un aralcène tel que 4-isobutylstyrène ou 2-méthoxy-6-vinylnaphtalène pour obtenir de l'ibuprofène ou du naproxène ou leurs esters, le nouveau ligand préféré étant, d'ordinaire, un mélange à parts égales de phosphine et d'oxyde de phosphine.

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