Water → (7-Nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol

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Reaction Steps

4-Nitrocatechol (30 g, 0.19 mol), lithium carbonate (36 g, 0.49 mol), and epichlorohydrin (38 mL, 0.49 mol) in DMF (180 mL) were heated to 70-85° C. for 47 hours. Water was added and the mixture extracted with EtOAc (3×). Concentration of the combined EtOAc extracts and crystallization from MeOH gave the title compound, first crop, 5.98 g, 14.7% yield, mp 131.8-135° C. and second crop, 1.64 g, 4% yield, mp 133.1-136.7° C., (lit. mp 131-134° C.). 1H NMR (d6-DMSO) δ 7.78 (1H, dd, J=8.9, 2.7 Hz); 7.72 (1H, d, J=2.7 Hz); 7.11 (1H, d, J=8.9 Hz); 5.16 (1H, br s); 4.48 (1H, dd, J=11.4, 2.1 Hz); 4.32-4.23 (1H, m); 4.17 (1H, dd, J=11.4, 7.4 Hz); 3.66 (2H, br s).

Provenance & Evidence