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

Temperature

140 °C

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.

1. temperatureOn cooling
2. washwashed with water (3×) and saturated sodium chloride
3. dry with materialThe organic solution was dried (MgSO4)
4. customevaporated to dryness under reduced pressure
5. additiona mixture of the desired product
6. customThe mixture was therefore chromatographed on silica gel
7. washeluting first with benzene

ORD record

ord-fb40f526989b4295be0e6a897f903bba

Source dataset

uspto-grants-1989_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04829099