Phenol → HCID 21432718, compound

Participants

Reaction Steps

A mixture of 6-ethylcinnolin-3-yl carboxylic acid (0.606 g.) and thionyl chloride (30 ml.) was heated under reflux on a steam bath for 20 minutes. The resulting solution was evaporated under reduced pressure to give a yellow crystalline solid, to which was added a solution of phenol (1.13 g.) in dry tetrahydrofuran (20 ml.). The mixture was heated under reflux on a steam bath for 2 hours. The resulting solution was evaporated and the residue was washed by decantation with ether (2× 50 ml.). The residual brown oil was dissolved in ethyl acetate (50 ml.) and washed successively with 5% w/v aqueous sodium bicarbonate (10 ml.) and water (2× 10 ml.). The ethyl acetate solution was dried (MgSO4), filtered and evaporated, and the residual oil was applied to the top of a silica column (30 g. Kieselgel 60). Elution with a 50% v/v mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.), and evaporation of the appropriate fractions, gave crude phenyl 6-ethylcinnolin-3-yl carboxylate. The product was recrystallised from aqueous ethanol, and then had m.p. 143°-145° C.

Provenance & Evidence