p-Toluenesulfonic acid → HCID 19047035, compound

Participants

Reaction Steps

The tertiary alcohol (3.9 g, 0.013 mol) obtained in Step C was refluxed for 3 h in toluene (60 mL) in the presence of a catalytic amount of p-toluenesulfonic acid (0.2 g). Azeotropic removal of water was achieved by employing a Dean-Starke trap. After cooling to room temperature, the toluene was removed under vacuum. The residue was taken up in ethyl acetate (200 mL) and washed with 10% aqueous sodium carbonate and brine (100 mL each). The dried (MgSO4) solution was concentrated to give 2.5 g (68% yield) of the title compound as white solid melting at 98°-104° C. 1H NMR (300 MHz, CDCl3) δ 7.91-7.94 (m,2H), 7.53 (s,1H), 7.43-7.46 (m,1H), 2.51 (s,3H).

Provenance & Evidence