Synthesis of 3-aryl-7-Hydroxy Isochromenes

Abstract

Phenol, anisole and resorcinol have been condensed with 4-hydroxyl

homophthalic acid in the presence of polyphosphoric acid to give

3-(4´-hydroxy phenyl)-; 3-( 4´-methoxyphenyl) and 3-(2´,4´ -dihydroxyphenyl)-

7-hydroxy isocoumarins. On treatment with aqueous sodium

hydroxide, 3-aryl isocoumarin yield the respective ω-(2´-carboxyl-

4´-hydroxyphenyl)-acetophenones. Sodium boro-hydride reduction of

acetophenones gives the corresponding dihydroisocoumarins. The

isocoumarins have been condensed with methyl magnesium iodide, ethyl

magnesium iodide and phenyl magnesium iodide to yield 3-(4´-hydroxy

phenyl), 3-(4´-methoxy phenyl)-, 3-(2´,4´-dihydroxy phenyl)-7-hydroxy-1,

1-dimethyl; 3-(4´-hydroxy phenyl)-, 3-(4´-methoxy phenyl)-3-(2´,4´dihydroxy

phenyl)-7-hydroxy-1,1-diethyl and 3-(4´-hydroxy phenyl)-,

3-(4´-methoxy phenyl) and 3-(2´,4´-dihydroxy phenyl)-7-hydroxy-1,1-diphenyl

ischromenes. The isocoumarins have been converted into iso-

quinolones with ammonia, ethyl amine and aniline.