Acetic Acid → 2-Methoxy-4-(2-nitroethyl)phenol

Participants

Reaction Steps

To sodium borohydride (4.3 g) suspended in a mixture of dioxane (85 ml) and ethanol (25 ml) at +10 to +15° C. is added 2-methoxy-4-(2-nitro-vinyl)-phenol in a mixture of dioxane (110 ml) and ethanol (50 ml). Thereafter the reaction mixture is stirred at room temperature for 2 hours. Acetic acid (4.5 ml) in water (130 ml) is then added carefully. The resulting mixture is evaporated to at about half of its volume. It is extracted with ethyl acetate (2×500 ml) washed with brine (2×100 ml) dried (MgSO4) and evaporated. 2-methoxy-4-(2-nitro-ethyl)-phenol is obtained as an oil which is purified by flash column chromatography on silica gel using ethyl acetate/hexane (1:1).

Provenance & Evidence