Dimethylformamide → 1,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzene

Participants

Reaction Steps

A mixture of 75.0 g. (0.397 mol.) of 4-bromoresorcinol, 95.1 ml. (0.80 mol.) of benzylbromide and 331 g. (2.4 mol.) of anhydrous potassium carbonate in 400 ml. of N,N-dimethylformamide is stirred for 12 hours at 25° C. and for 4 hour at 85° C. The reaction mixture is cooled and added to one liter of ice-200 ml. pentane-100 ml. ether. The organic phase is washed with three 500 ml. portions of water, dried over magnesium sulfate and evaporated to an oil. The oil is rapidly chromatographed on 400 g. of silica gel eluted with 20% ether-pentane to yield 80 g. of oil. The chromatographed oil is crystallized from pentane at 0° C. to yield 45.0 g. (30%) of the title compound, M.P. 37°-38° C.

Provenance & Evidence