Hydrochloric Acid → HCID 57320364, compound

Participants

Reaction Steps

To a solution of ethyl benzoylformate (520 mg, 2.92 mmoL) in dry benzene 5 mL) was added PCl5 (608 mg, 1.0 equiv). After stirring at reflux for 16 h TLC analysis indicated that all the starting material appeared consumed. The solvent was removed in vacuo and the crude dichloride (Rf=0.61 6:1 hexane/ethyl acetate) was mixed with 4-methyl-catechol (724 mg 2.0 equiv) and heated to 175° C. until HCl evolution ceased (ca. 20 min). The mixture was cooled to rt and the glue-like material was dissolved in diethyl ether and washed several times with 1N NaOH and then brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo and the residue was chromatographed on a silica column eluting with hexane/ethyl acetate (20:1). Removal of the solvent afforded 130 mg (16%) of the titled compound. Rf=0.57 (6:1 hexane/ethyl acetate).

Provenance & Evidence