Vinyl propanoate → 2-Hydroxyphenyl 2-vinyloxyphenyl ketone

Participants

Reaction Conditions

Reaction Steps

To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (3.81 g, 5.7 mmol) and sodium carbonate (24.9 g, 0.23 mol)) in toluene (280 ml) were added 2,2′-dihydroxybenzophenone (0.19 mmol) and vinyl propionate (0.75 mol), followed by stirring at 100° C. in an atmosphere of argon gas for 10 hours. The reaction mixture was analyzed by gas chromatography to find that bis(2-vinyloxyphenyl) ketone [i.e., bis(2-vinyloxyphenyl)methanone] and 2-hydroxyphenyl 2-vinyloxyphenyl ketone [i.e., 2-hydroxyphenyl(2-vinyloxyphenyl)methanone] were formed in yields of 82% and 5%, respectively, with a conversion from 2,2′-dihydroxybenzophenone of 99%.

Provenance & Evidence