Ethylene Glycol → 2-(3-nitrophenyl)-1,3-dioxolane

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Reaction Steps

A solution of m-nitrobenzaldehyde 69d (20 g, 0.13 mol), ethylene glycol (9.0 g, 0.15 mol) and p-TsOH (catalytic amount) in toluene (50 mL) was refluxed under a Dean-Stark trap for 12 hr. The solution was then cooled to room temperature, diluted with toluene (20 mL) and washed with NaOH solution (1 M, 20 mL), water, brine and then dried with MgSO4. Evaporation of the solvent under reduced pressure gave 2-(3-Nitro-phenyl)-[1,3]dioxolane (24 g, 95%): 1H NMR (CDCl3) δ 4.11 (d of mult, ethylenedioxy, 4H), 5.78 (s, 1H), 7.56 (t, J=8 Hz, 1H), 7.80 (d of mult, J=8 Hz), 8.22 (d of mult., 1H), 8.35 (m, 1H). 13C NMR (CDCl3) δ 148.3, 140.5, 132.8, 129.5, 124.1, 121.7, 102.3, 65.6.

Provenance & Evidence