4-Nitrobenzoic Acid → 1,2-Ethanediol, 1-(4-nitrobenzoate)

Participants

Reaction Conditions

Reaction Steps

A mixture of p-nitrobenzoic acid (33.4 g, 0.2 mole), ethylene carbonate (19.4 g, 0.22 mole) and tetraethylammonium iodide (9.6 g, 0.036 mole) was heated at 140° C. for 45 minutes. On cooling, the mixture was dissolved in ethyl acetate (500 ml) and washed with water (3×) and saturated sodium chloride. The organic solution was dried (MgSO4) and evaporated to dryness under reduced pressure. The residue was shown to be a mixture of the desired product and a small amount of the diester product, bis-(4-nitrobenzoyl)-ethylene glycol, by TLC (silica gel, ethyl acetate as mobile phase; Rf 's=0.5 and 0.7, respectively). The mixture was therefore chromatographed on silica gel, eluting first with benzene and then with chloroform to give hydroxyethyl p-nitrobenzoate (31 g) as a pale yellow solid, m.p. 77°-78° C., which was homogeneous by TLC.

Provenance & Evidence