p-Toluenesulfonic acid → 1-Phenyl-cycloheptene

Participants

Reaction Steps

In a round bottom flask fitted with a Dean Stark and a condenser was added a solution of alcohol (obtained above) in benzene (90 mL) and a catalytic amount of p-toluenesulfonic acid. The reaction mixture was refluxed for 3 hours and then cooled to room temperature. The mixture was washed with water (30 mL), brine (30 mL), dried (MgSO4), and concentrated to afford the corresponding alkene 90 (3.1 g, 84% yield). 1H NMR (400 MHz, CDCl3: δ 7.70-7.35 (m, 9H), 6.15 (t, J=8.0 Hz, 1H), 2.75-2.68 (m, 2H), 2.43-2.35 (m, 2H), 1.80-1.60 (m, 6H).

Provenance & Evidence