4-Chlorodehydromethyltestosterone synthesis

In a dry reaction flask equipped with a reflux condenser (open to air), combine Methylclostebol and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). Then, add the solvent benzene to the reaction system and stir to ensure homogeneity. Slowly add p-toluenesulfonic acid to the mixture. Reflux the resulting reaction mixture with stirring for 20 hours. Upon completion of the reaction, add water and ethyl acetate to the system. Collect the organic phase, dry it over anhydrous sodium sulfate, and concentrate the filtrate under reduced pressure. Purify the residue by silica gel column chromatography to obtain the target product, 4-chlorodehydro-methyltestosterone.