Hydrochloric Acid → HCID 14180962, compound

Participants

Reaction Steps

A solution of 4-methoxybenzeneacetic acid (8.3 g) in dry THF (250 ml) was treated with triethylamine (6.9 ml) and wooled in a salt/ice-bath with stirring under a nitrogen atmosphere. Pivaloyl chloride (6.1 ml) was added and stirring continued for 1 h. A further aliquot of triethylamine (6.9 ml) was added followed by p-nitrophenethylamine hydrochloride (10 g). The resultant suspension was warmed to room temperature and stirred for 19.5 h (overnight). The reaction mixture was acidified to pH 1 using hydrochloric acid solution (2N; 30 ml) and the resultant solution was extracted with EA (1×250 ml, 1×100 ml). The combined organic extracts were washed with 8% NaHCO3 solution (200 ml), dried (MgSO4) and evaporated under reduced pressure to give a brown oil. Purification by `flash` chromatography, ER:CH2Cl2 (4:1) gave the title compound as a pale yellow solid (7.4 g) m.p. 109°-110°.

Provenance & Evidence