Reaction #43964

Reaction equation

sodium carbonate

α,α,α′,α′-tetramethyl-1,4-benzenedimethanol

vinyl acetate

1-(1-hydroxy-1-methylethyl)-4-(1-methyl-1-vinyloxyethyl)benzene

→

1,4-bis(1-methyl-1-vinyloxyethyl)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 α,α,α′,α′-tetramethyl-1,4-benzenedimethanol (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-(1-hydroxy-1-methylethyl)-4-(1-methyl-1-vinyloxyethyl)benzene and 1,4-bis(1-methyl-1-vinyloxyethyl)benzene were formed in yields of 11% and 62%, respectively, with a conversion from α,α,α′,α′-tetramethyl-1,4-benzenedimethanol of 95%.

Source