Process for the preparation of stilbenedicarboxylate esters

Details Process for the preparation of stilbenedicarboxylate esters Process for the preparation of stilbenedicarboxylate esters

C - Chemistry, Metallurgy

07

C

C07C 69/76 (2006.01) C07C 67/343 (2006.01)

Patent

CA 2214655

Disclosed is a process for the preparation of 4,4'-stilbenedicarboxylate esters by a 4-step process starting with an alkyl p-formylbenzoate and utilizing intermediate phosphite and phosphonate compounds. The steps comprise: (1) preparing an alkyl p-(hydroxymethyl)benzoate by hydrogenating an alkyl p-formylbenzoate; (2) contacting the alkyl p-(hydroxymethyl)benzoate of step (1) with a trialkyl phosphite to obtain a phosphite ester compound having formula (IV); (3) contacting the phosphite ester of step (2) with a catalytic amount of iodine to rearrange the phosphite ester to the corresponding phosphonate ester; and (4) contacting the phosphonate ester compound of step (3) with an alkyl p-formylbenzoate in the presence of an alkali metal alkoxide and an inert solvent to obtain the dialkyl 4,4'-stilbenedicarboxylate.

Cette invention concerne un procédé de préparation d'esters de 4,4'-stilbènedicarboxylate au moyen d'un processus en quatre étapes démarrant avec un p-formylbenzoate d'alkyle et utilisant des composés phosphite et phosphonate intermédiaires. Ces étapes consistent (1) à préparer un p-(hydroxyméthyl)benzoate d'alkyle par hydrogénation d'un p-formylbenzoate d'alkyle, (2) à mettre en contact le p-(hydroxyméthyl)benzoate d'alkyle de l'étape (1) avec un phosphite de trialkyle de façon à obtenir un composé ester de phosphite représenté par la formule (IV), (3) à mettre en contact l'ester de phosphite de l'étape (2) avec une quantité catalytique d'iode de façon à réorganiser l'ester de phosphite en ester de phosphonate correspondant, et (4) à mettre en contact le composé ester de phosphonate de l'étape (3) avec un p-formylbenzoate d'alkyle en présence d'un alkoxyde de métal alcalin et d'un solvant inerte de façon à obtenir le 4,4'-stilbènedicarboxylate de dialkyle.

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