Hydrochloric Acid → 4-(4-Ethenylphenoxy)benzene-1,3-diamine

Participants

Reaction Steps

1-[4-Vinylphenoxy]-2,4-dinitrobenzene (9.0 g, 31 mmol) was dissolved in 100 ml ethanol/tetrahydrofuran (1:1). In succession, tin(II)chloride (70.9, 310 mmol), and 10N HCl (37.7 ml, 377 mmol) were added. The solution was stirred at room temperature 16 h. The reaction mixture was poured into a separatory funnel containing 150 ml ice-cold water followed by the addition of 20% KOH (ice-cold, 629 g). The mixture was extracted with ether (3×100 ml). The combined organic phases were washed with water (3×100 ml) and brine, dried with solid MgSO4 and concentrated. Column chromotography yielded 4.5 g product. The product was crystallized from 40% ethyl acetate in hexane. 1H NMR (CDCl3): 7.32 (d, 2H, J=8.5 Hz), 6.88 (d, 2H, J=8.6 Hz), 6.73 (d, 1H, J=8.3 Hz), 6.66 (dd, 1H, J=17.3, 11.9 Hz), 6.15 (d, 1H, J=2.9 Hz), 6.08 (dd, 1H, J=2.4, 8.2 Hz), 5.61 (dd, 1H, J=17.6 Hz, 0.8 Hz), 5.14 (d, 1H, J=10.9 Hz), 4.38 (br s, 4H).

Provenance & Evidence