4-Nitrophenol → Isopropenyl p-nitrophenyl carbonate

Participants

Reaction Steps

Isopropenyl chloroformate (5.0 g) was added to an ice cold suspension of p-nitrophenol in chloroform (100 mL). To the stirred reaction mixture, pyridine (3.32 g) 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 overnight. The reaction mixture was washed with water, IN HCl, ice-cold 1% aqueous sodium hydroxide, water and brine. The organic layer was dried over sodium sulfate and evaporated. The solid residue weighed at 8.7 g. It was crystallized from benzene-hexane m.p. 71-72° . 1H NMR (CDCl3) δ 2.05 (3H, s), 4.82 (2H, s), 7.44 (2H, d) and 8.01 (2H, d); 13C NMR (CDCl3) δ19.59, 102.49, 128.25, 128.79, 131.29, 139.8, 153.07 and 163.84; 1R (KBr) 1770, 1521, 1352, 1266, 1207, 859 cm-1.

Provenance & Evidence