Hydrogen Peroxide → (4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one

Participants

Reaction Conditions

Reaction Steps

18.66 kg of oxalic acid is dissolved in water, 84.8 kg of thebaine is added, and after it has dissolved, 19.50 kg of 88% formic acid and 42.4 kg of 30% hydrogen peroxide are added. The reaction mixture is stirred at 25° C. until total conversion of thebaine (determined by capillary electrophoresis; capillary 50 cm×0.05 mm, electrolyte 100 mM TRJS/phosphate, pH 2.7, 5 mM dimethoxy-β-cyclodextrin, temperature 25° C. 30 kV; thebaine migration time 5.6 min). The reaction mixture is cooled down to 5° C., 10% aqueous solution of KOH is added with stirring until pH of 9.2. Precipitated crystals of 14-hydroxycodeinone are centrifuged off, washed with water and dried. Ca. 76 kg of 14-hydroxycodeinone (89%) is obtained.

Provenance & Evidence