60034-94-8Relevant academic research and scientific papers
Isocoumarins : Part III - Synthesis of Methyl- and Methylenedioxydihydroisocoumarins and a New Synthesis of (+/-)-5-Methylmellein
Bhide, Bhaskar H.,Shah, Kashmira K.
, p. 9 - 12 (2007/10/02)
o-Lithio-N-methylbenzamide upon condensation with propylene oxide gives 3-methyldihydroisocoumarin.Similarly o-lithio-N-methyl-p-toluamide upon condensation with ethylene oxide and propylene oxide give 6-methyl- and 3,6-dimethyldihydroisocoumarin.A similar condensation of o-lithio-N-methyl-m-toluamide with ethylene oxide gives 5-methyldihydroisocoumarin but condensation with propylene oxide gives 3,5-dimethyl- and 3,7-dimethyldihydroisocoumarins.The method has been used to synthesize (+/-)-5-methylmellein.The synthesis of 5,6-methylenedioxydihydroisocoumarin from o-lithio-N-methylpiperonylamide is also described. 3-Methyl-6,7-methylenedioxydihydroisocoumarin has been synthesized by an acid-catalyzed cyclization reaction.
