Hydrochloric Acid → 3-Amino-4-chlorophenyl 3,5-di-t-butyl-4-hydroxybenzoate

Participants

Reaction Steps

Iron metal powder (50.2 g; 0.897 mole) and 10M-hydrochloric acid (92 ml; 0.92 mole) were added alternatively over 11/2 hr. to a mixture, of the nitro compound (60.6 g; 0.149 mole) from (a), tetrahydrofuran (520 ml) and water (52 ml), heated under reflux. Heating was continued for a further 31/2 hr. after which the mixture was filtered. The filtrate was evaporated to dryness and the residue partitioned between toluene (500 ml) and water (400 ml). The layers were separated and the toluene solution filtered through kieselguhr, dried and evaporated to give a solid. This material was crystallized from methanol (100 ml) to give the product (41 g; 75%) as a white solid, m.p. 64°-66° C.

Provenance & Evidence