Dimethylformamide → 4'-Benzyloxy-2'-hydroxyacetophenone

Participants

Reaction Steps

Fifty grams of 2,4-dihydroxyacetophenone were dissolved in 250 ml. of dimethylformamide and the solution was cooled to 0° C. by means of an external ice-bath. After the addition of 15 grams of a 50% oil dispersion of sodium hydride, 40 ml. of benzyl chloride were added in a dropwise fashion and the reaction was allowed to warm to room temperature. After stirring overnight, the reaction mixture was added to 700 ml. of ethyl acetate. The organic phase was washed with 1000 ml. of 1N hydrochloric acid and twice each with 1000 ml. of a saturated sodium chloride solution. The organic layer was dried, and the solvent removed in vacuo. The oily residue was treated with 100 ml. of methanol and 50 ml. of hexane. The desired 2-hydroxy-4-benzyloxyacetophenone (36.7 grams) was recovered by filtration.

Provenance & Evidence