Naphthalen-1-ethanol → 2-(1-Naphthyl)ethyl 3,4-dihydroxycinnamate

Participants

Reaction Steps

Reaction of caffeic acid and 2-(1-naphthyl)ethanol as outlined in method A except that the reaction time was increased to 6 days, provided product 67H-148-A as a snow-white solid in 21% overall yield: mp 165°-168° C.; 1H NMR (DMSO-d6) δ:8.21 (d, 1H, J=8.1 Hz), 7.97-7.94 (m, 1H), 7.84 (t, 1H, J=5 Hz), 7.64-7.39 (m, 5H), 7.03 (d, 1H, J=1.8 Hz), 6.99 (dd, 1H, J=1.8 Hz & 8.1 Hz), 6.23 (d, 1H, J=15.9 Hz), 4.44 (t, 2H, J=7.0 Hz), 3.45 (t, 2H, J=7.0 Hz); FABMS (NBA, -VE) m/z 333 (M--H). Anal. (C21H18O4.1/4H2O) C, H.

Provenance & Evidence