Water → HCID 54245544, compound

Participants

Reaction Steps

A mixture of 4-hydroxy-3-methoxybenzyl alcohol (76.1 g) and sodium cyanide (19.9 g) in dimethylformamide (250 ml) is stirred under an atmosphere of nitrogen for 3 hours at +120° C. The reaction mixture is cooled to +90° C. and 1-chloro-4-(3-chloro-propenyl)-benzene is added. The mixture is stirred at said temperature for 2 hours. After cooling it is poured into water (1000 ml) and extracted with ethyl acetate (2×500 ml). The organic layers are washed with brine (2×500 ml), dried (MgSO4) and evaporated. The residue is purified by flash column chromatography using silica gel and ethyl acetate/hexane (1:3). The product obtained is dissolved in methanol (400 ml) and hydrogenated over Raney-cobalt at +40° C. and 100 bar. Water (300 ml) and ethyl acetate (200 ml) are added. After filtration the reaction mixture is extracted with ethyl acetate (2×500 ml). The organic layers are washed with brine (2×200 ml), dried (K2CO3) and evaporated. 2-{4-[3-(4-Chloro-phenyl)-allyloxy]-3-methoxy-phenyl}-ethylamine is obtained.

Provenance & Evidence