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 Steps

Thebaine (100.0 g dry weight) was dissolved in 85% formic acid (252.3 g). 30% Hydrogen peroxide (43.6 g) was added over a period of about two hours. The mixture was stirred for three hours. Ammonium hydroxide solution was added to the mixture to increase the pH to 8–9. The solid precipitate was filtered and washed with water and ethanol. The solid was dried on the filter and in an oven. The product was 14-hydroxycodeinone (150.52 g damp, 75.32 g dry weight, 75% yield).

Provenance & Evidence