Reaction #43966

Reaction equation

1-hydroxy-3,5-bis(vinyloxy)benzene

sodium carbonate

1,3,5-trihydroxybenzene

vinyl acetate

1,3-dihydroxy-5-vinyloxybenzene

→

1,3,5-tris(vinyloxy)benzene

Solvents

toluene

Conditions

Procedure

To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (67 mg, 0.1 mmol) and sodium carbonate (640 mg, 6 mmol) in toluene (5 ml) were added 1,3,5-trihydroxybenzene (5 mmol) and vinyl acetate (2.15 g, 25 mmol), followed by stirring at 100° C. in an atmosphere of argon gas for 6 hours. The reaction mixture was analyzed by gas chromatography to find that 1,3-dihydroxy-5-vinyloxybenzene, 1-hydroxy-3,5-bis(vinyloxy)benzene, and 1,3,5-tris(vinyloxy)benzene were formed in yields of 5%, 4%, and 18%, respectively, with a conversion from 1,3,5-trihydroxybenzene of 29%.

Source