Sulfuric Acid → 1-(2-Methylphenyl)-1-phenyl-1-propene

Participants

Reaction Steps

TLC: rf=0.50 (SiO2; n-heptane/THF=7:3). 1-(2-Methylphenyl)-1-phenyl-1-propanol (10.4 g, 46 mmol) was dissolved into isopropanol (100 ml) and a 4 N sulphuric acid solution (50 ml) was added. The reaction mixture was heated at reflux temperature for 18 h and cooled to room temperature. Water (300 ml) was added and the mixture was extracted with dichloromethane (2×200 ml). The combined organic extracts was washed with a diluted sodium bicarbonate solution, dried (Na2SO4) and the solvent evaporated in vacuo to give 9.0 g (91%) of 1-(2-methylphenyl)-1-phenyl-1-propene. To a solution of 1-(2-methylphenyl)-1-phenyl-1-propene (9.0 g, 43 mmol) in carbon-tetrachloride (40 ml), N-bromosuccinimide (7.7 g, 43 mmol) and benzoylperoxide (0.1 g) were added. The reaction mixture was heated at reflux temperature for 18 h. The cooled reaction mixture was filtered through silica gel and the solvent evaporated in vacuo to give 9.3 g (76 %) of 3-bromo-1 (2-methylphenyl)-1-phenyl-1-propene.

Provenance & Evidence