N,N-Dimethylaniline → Resveratrol

Participants

Reaction Conditions

Reaction Steps

In a 3 lit. round-bottomed flask equipped with a thermometer are added aluminum chloride (390.35 gm) and N, N-dimethylaniline (413.10 gm) maintaining the temperature at 40-50° C.(exothermic). To this solution, (E)-1-[4-(benzyloxy)phenyl]-2-[3,5-bis(benzyloxy)phenyl]ethene (243 gm) in dichloromethane (800 ml) is added and stirred for further 0.75 hour. After the reaction is over, the reaction mixture is quenched into dil. hydrochloric acid at 0-5° C. and extracted with ethyl acetate. The organic layer is charcoalized and concentrated to get pure (E)-1-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)ethene (trans-Resveratrol) in the exclusive trans form. Mp 257-259° C. 1H NMR (DMSO-d6, 400 MHz) δ 6.11 (t, J=1.8 Hz, 1H), 6.38(d, J=1.8 Hz, 2H), 6.75 (d, J=8.5 Hz, 2H), 6.82(d, J=16.3 Hz, 1H), 6.92(d, J=16.3, 1H), 7.39(d, J=8.4 Hz, 2H); Mass M/e:228.2

Provenance & Evidence