117970-24-8Relevant articles and documents
TOTAL SYNTHESIS OF (+/-)-HYDRANGENOL
Napolitano, Elio,Ramacciotti, Antonella,Fiaschi, Rita
, p. 101 - 104 (2007/10/02)
The title compound 8 has been synthesized in five steps and in about 33percent overall yield from 3-methoxyphenylacetic acid, 1.Acid 1 was condensed with anisole in polyphosphoric acid to give 3',4-dimethoxydeoxybenzoin, 2, which was converted to the ethylene acetal 3.The latter was metallated with buthyllithium and carbonated giving crude 3',4-dimethoxydeoxybenzoin-2'-carboxylic acid, 4, from which 3,4-dihydro-8-methoxy-3-(4'-methoxyphenyl)isocoumarin, 7, was obtained either by reduction with sodium borohydride and dehydration, or dehydration to 8-methoxy-3-(4'-methoxyphenyl)isocoumarin, 6, and catalytic hydrogenation.Finally, demethylation of 6 to 8 was performed with boron tribromide.