4-Nitrophenol → 2-Propanol, 1,3-bis(p-nitrophenoxy)-

Participants

Reaction Steps

A solution of 1 g (7.2 mmol) of 4-nitrophenol, 0.28 ml (3.6 mmol) of epichlorohydrin, and 0.16 g (3.96 mmol) of sodium hydroxide in 2 ml of dimethylformamide was heated at 110° C. for 1 h. The solvent was removed in vacuo, and the residue was purified by flash chromatography using chloroform to give 0.97 g (81%) of the desired compound (Rf 0.42, 40% ethyl acetate in chloroform). 1H NMR (CDCl3) δ2.54 (d, 5 Hz, 1H), 4.28 (dd, J=10, 6 Hz, 2H), 4.29 (dd, J=10, 5 Hz, 2H), 4.50 (br sextet, J=6 Hz, 1H), 7.0-7.05 (m, 4H), 8.2-8.3 (m, 4H). Mass spectrum (M+NH4)+ =352.

Provenance & Evidence