Sodium Cyanide → 3,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)phenylacetonitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of sodium cyanide (0.23 g, 4.69 mmol) in H2O (2 mL) at room temperature was added a solution of 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)benzyl bromide (0.85 g, 2.34 mmol) in ethanol (5 mL). The reaction mixture was heated at 80° C. for 2 h, cooled to room temperature, and poured into ice water (100 mL). The mixture was stirred for 1 h and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:4) to afford 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)phenylacetonitrile as a brown solid (0.64 g, 85%, m.p.: 56-58° C.): 1H NMR (300 MHz, CDCl3): δ 7.07 (s, 2 H), 6.78 (d, J=3.3 Hz, 1 H), 6.68 (d, J=9.0 Hz, 1 H), 6.35 (dd, J=3.0, 8.7 Hz, 1 H), 3.80 (s, 3 H), 3.73 (s, 2 H), 3.40-3.25 (m, 1 H), 2.16 (s, 6 H), 1.19 (d, J=7.2 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; mobile phase=ethyl acetate-hexanes (1:4); Rf=0.5.

Provenance & Evidence