4-Nitrophenol → Isopropenyl p-nitrophenyl carbonate

Participants

Reaction Steps

Isopropenyl chloroformate (5.0 g, 41.5 mmol) was added to an ice cold suspension of p-nitrophenol (6.3 g, 45.6 mmol) in chloroform (100 mL). To the stirred reaction mixture, pyridine (3.32 g, 41.5 mmol) was added dropwise over 20 minutes. After stirring at ice bath temperature for 15 minutes, the reaction mixture was allowed to warm up and stirred at room temperature for 16 hours. The reaction mixture was washed with water, 1N HCl, ice-cold 1% aqueous sodium hydroxide, water and brine. The organic layer was dried (MgSO4) and the solvent was evaporated. The solid residue was subsequently crystallized from hexane to provide the title compound (7.8 g, 84% yield): 1H NMR (CDCl3, 300 MHz) δ 2.05 (s, 3H), 4.82 (t, 1H, J=1.0 Hz), 4.96 (d, 1H, J=2.0 Hz), 7.40-7.46 (m, 2H), 8.27-8.32 (m, 2H).

Provenance & Evidence