18-Crown-6 → HCID 57687132, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2,5-dimethoxy-3-hydroxynitrobenzene (2.0 g, 8.43 mmol), 18-crown-6 (2.97 g, 8.43 mmol) and bromomethyl dioxolane (4.22 g, 25.3 mmol) was added DMF (60 ml). The solution was then heated for a total of 1.5 h in the CEM microwave at 140° C., initial voltage=300 W. The solution was poured on to a mixture of sat. NaHCO3 and Et2O, the layers separated and the aqueous extracted with Et2O. The combined organic layers were washed with water (4×50 ml), 1M HCl (50 ml) and brine (2×50 ml), dried over MgSO4 filtered and evaporated. Hexanes were added to the solid residue and the resulting suspension stirred for 1 h. The product was isolated by filtration and dried in a vacuum oven to afford the title compound (1.45 g, 57%). m/z 286 [M+H]+.

Provenance & Evidence