1,5-Dihydroxynaphthalene → 1,5-Bis(vinyloxy)naphthalene

Participants

Reaction Conditions

Reaction Steps

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 1,5-dihydroxynaphthalene (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-hydroxy-5-vinyloxynaphthalene and 1,5-bis(vinyloxy)naphthalene were formed in yields of 15% and 13%, respectively, with a conversion from 1,5-dihydroxynaphthalene of 30%.

Provenance & Evidence