Toluene → 2,6-Di(propan-2-yl)-4-(prop-2-en-1-yl)aniline

Participants

Reaction Steps

N-allyl-2,6-diisopropyl aniline (18.33 g, 0.084 mol) and ZnCl2 (13.6 g, 0.1 mol) were added to a 100 ml toluene solution. This solution was refluxed for 5 hr and then poured into a NaOH aqueous solution. Extraction with Et2O (3×50 ml) and distillation (79.93 Pa, 98° C.) yielded 13.0 g (70.9%) of 4-allyl-2,6-diisopropyl aniline. Nd30=1.5340, 1H-NMR (ppm,CDCl3): δ=6.85(s, 2H, Ph-Hm),5.98(m, 1H, CH═C),5.09(d, 1H, C═C—Htrans),5.03(d, 1H, C═C—Hcis),3.6(br, 2H, NH2), 3.30(d, 2H, CH2—C═C), 2.92(m, 2H, CH(Me)2), 1.26(d, 12H, C(CH3)2)

Provenance & Evidence