反应详情

A solution containing 2,6-diisopropyl aniline (35.4 g, 0.2 mol) and allyl chloride (7.6 g, 0.10 mol) was refluxed for 12 hr and then poured into water (400 ml). Adding an aqueous NaOH solution to the reaction mixture made the mixture basic. After extraction with diethyl ether (3×50 ml) and distillation (73.25 Pa, 92° C.), 18.33 g (84.3%) of N-allyl-2,6-diisopropyl aniline was isolated. Nd30=1.5205. 1H-NMR (ppm,CDCl3): δ=7.10(d, 2H, Ph-Hm), 6.81(t, 1H, Ph-Hp), 6.05(m, 1H, CH═C), 5.34(d, 1H, C═C—Htrans), 5.16(d, 1H, C═C—Hcis), 3.71(broad, 1H, NH), 3.50(d, 2H, CH2—C═C), 3.26(m, 2H, CH(Me)2), 1.28(d, 12H, C═C(CH3)2).

1. temperaturewas refluxed for 12 hr
2. extractionAfter extraction
3. distillationwith diethyl ether (3×50 ml) and distillation (73.25 Pa, 92° C.)