Highly regioselective one-pot synthesis of 7-hydroxy-6-methylphthalide from 3-hydroxy-4-methylbenzylalcohol
7-Hydroxy-6-methylphthalide 2 was synthesized with high regioselectivity and moderate yield using a novel one-pot synthesis that employed 3-hydroxy-4-methylbenzylalcohol 1 and formaldehyde in the presence of tin(IV) chloride as catalyst and triethylamine
Pyrolysis of O-Allyl Salicylic Amides and Esters, and Related Compounds: Foemation of Isoindolones and Phthalides
Flash vacuum pyrolysis of O-allyl salicylic alkylamides and alkyl esters gives isoindolones and phthalides, respectively, in low (20-40percent) yield.The mechanism involves generation of the phenoxyl radical, regiospecific hydrogen-atom transfer from the alkylamide (or alkyl ester) group and cyclization.A similar sequence was observed with thiophenoxyl radicals.
Black, Michael,Cadogan, J. I. G.,McNab, Hamish
p. 155 - 160
(2007/10/02)
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