Mitsonobu reaction of cannabidiol. Synthesis of water-soluble cannabidiol derivatives

Abstract

Mitsunobu reactions of cannabidiol (CBD) as the acid component and primary alcohols, for example benzyl, allyl, propargyl and methyl glycolate as the alcohol component gave the corresponding bis-alkylated CBD derivatives which were also obtained by alkylating CBD with the corresponding alkyl bromides. Alkylation of CBD with methyl bromoacetate followed by saponification of the two ester moieties and neutralization of the di-carboxylic acid afforded a water-soluble CBD bis-acetate bis-potassium salt.