Ammonia → 1,4-Bis(3,4-dimethoxyphenyl)-2,3-dimethyl-1,4-butanedione

Participants

Reaction Conditions

Reaction Steps

To 100 ml of liquid NH3 and 100 mg FeCl3, 1 g of sodium was added and stirred for 1 hr at -40° C. To that 7.7 g of 3,4-dimethoxypropiophenone was added and stirred for 1/2 hr. Eleven g of α-bromo-3,4-dimethoxypropiophenone was then added and stirring continued for 11/2 hrs. At this point, 11 g of ammonium chloride and 200 ml of methylene chloride was added and the temperature allowed to rise to room temperature. Filtration, evaporation and crystalization of the residue from methanol gave 14.5 g of racemic-2,3-bis(3,4-dimethoxybenzoyl)butane as a white solid. NMR (CDCl3) δ1.32(6H, d, J=7Hz), 3.92 and 3.94 (6H each, s, OCH3, 6.8-7.8 (6H, ArH); m.p. 141°-142° C.

Provenance & Evidence