Sodium Iodide → 1-{2-Hydroxy-3-propyl-4-[3-(4-nitrophenoxy)propoxy]phenyl}ethanone

Participants

Reaction Conditions

Reaction Steps

To sodium hydride (6.1 g, 50% dispersion) in dry dimethylformamide (200 ml) was added 2,4-dihydroxy-3-propylacetophenone (24.6 g) in dimethylformamide (20 ml), dropwise with stirring under nitrogen. The resulting solution was heated to 100° C. and 4-nitro-1-(3-chloropropoxy)benzene (27.3 g) and sodium iodide (19.0 g) were added rapidly. The reaction mixture was left to stir over night at 100° C., cooled and evaporated under reduced pressure to a brown oil. The oil was taken up in water, extracted with dichloromethane (×2), washed with aqueous sodium hydroxide (2N), then aqueous sodium thiosulphate, dried over magnesium sulphate, filtered and evaporated under reduced pressure to a dark brown solid. The solid was recrystallised from methanol, with charcoaling, to give pale yellow needles of product, m.p. 98° C.

Provenance & Evidence