Acetic Anhydride → 2-Acetylfluorenon

Participants

Reaction Steps

A method of producing the bisulphite compound of 2-fluorenonyl-glyoxal, viz, the active principle of said medicinal preparation, consists in that fluorene is acylated by dichloroacetyl chloride in the presence of aluminum chloride and phosphoryl chloride in an organic solvent, the resultant 2-ω-dichloroacetylfluorene is oxidized by the salts of chromic acid in an acetic-acid medium at 50°-90° C into 2-ω-dichloroacetylfluorenone which is made to interact with morpholine at 50°-98° C to form 2-ω-dimorpholinoacetylflourenone, or otherwise, fluorenone is acylated by acetic anhydride in an organic solvent in the presence of aluminum chloride, the resultant 2-acetylfluorene is oxidized by chromic acid or by the salts thereof in an acetic acid medium at 50°-90° C to obtain 2-acetylfluorenone which is brominated in an organic solvent at 60°-110° C, the resultant 2-ω-dibromoacetylfluorenone is reacted with morpholine at 50°-98° C to form 2-ω-dimorpholinoacetylfluorenone the latter is hydrolyzed by dilute mineral acids at 20°-100° C into 2-fluorenonyl-glyoxal hydrate which is then made to react with sodium bisulphite in an aqueous-alcohol medium at 60°-80° C to isolate the final product.

Provenance & Evidence