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

Participants

Reaction Steps

To sodium borohydride (1.93 g, 51.2 mmol) suspended in ethanol (15 ml) at +10 to +15° C. is added a solution of 2-methoxy-4-(2-nitro-vinyl)-phenol (10.0 g, 51.2 mmol) in tetrahydrofuran (100 ml) over 1 h. Thereafter the reaction mixture is stirred at room temperature for 30 minutes. Acetic acid (4 ml) in water (100 ml) is then added carefully. The resulting mixture is evaporated to at about a quarter of its volume. It is extracted with ethyl acetate (1×100 ml, 1×50 ml) washed with brine (2×50 ml) dried (Na2SO4) and evaporated. 2-methoxy-4-(2-nitro-ethyl)-phenol (9.64 g) is obtained as an oil, which is purified by kugelrohr distillation (+150° C., 0.02 torr) yielding 7.3 g (72%) of purified material.

Provenance & Evidence