ANALYSIS OF 3,4-METHYLENEDIOXYPHENYL-2-PROPANONE AND 3,4-METHYLENEDIOXYAMPHETAMINE PREPARED FROM ISOSAFROLE

The intermediates, products, and by-products obtained in the synthesis of MDA from isosafrole are identified by gas chromatography-mass spectrometry. The initial oxygenation of the conjugated double bond in isosafrole produces a number of products, and the product distribution varies with the reaction solvent. If acetone is used as a cosolvent, the major product is the diol acetonide, while without acetone the product mixture contains the diol, the ketone (methylenedioxyphenyl-2-propanone, MDP-2-P), and mono- and diformates of the diol. These oxygenated products, upon treatment with sulfuric acid, are all converted to the expected ketone, MDP-2-P. Amination of MDP-2-P with formamide (Leuckart conditions) yields the desired amine, MDA, and a pyrimidine by-product, 4-methyl-5-(3,4-methylenedioxyphenyl)pyrimidine, which is characteristic of these reaction conditions. © 1994 Oxford University Press.