Hydrochloric Acid → Ethyl 2-(3-aminophenoxy)acetate

Participants

Reaction Steps

A mixture of ethyl 3-nitrophenoxyacetate (10 g) in ethanol (200 ml), iron powder (10 g) and concentrated hydrochloric acid (4.8 ml) was heated at reflux for 5 hours. The solid residue was removed by filtration whilst the mixture was hot, and was washed with warm ethanol. The solvent was evaporated and the residue partitioned between sodium bicarbonate solution and methylene chloride. The aqueous layer was separated and extracted with fresh methylene chloride. The combined organic extracts were dried (MgSO4) and evaporated. The residue was eluted through silica using a 5:3 mixture of hexane and ethyl acetate as eluent to give ethyl 3-aminophenoxyacetate as an orange oil in 66% yield;

Provenance & Evidence