Resorcinol → Phenol, 3-(2-quinolinylmethoxy)-

Participants

Reaction Steps

To a solution of 15.0 g (70.1 mm) of 2-chloromethylquinoline hydrochloride and 7.71 g (70.1 mm) of resorcinol in 50 ml ethanol under nitrogen is added over 30 minutes dropwise a solution of 9.1 g (140.0 mm) potassium hydroxide in 50 ml ethanol. After addition is complete the reaction mixture is refluxed for 2 hours. The solution is allowed to come to room temperature; the precipitate is then filtered off. The mother liquor is evaporated and the residue is triturated with methylene chloride. Evaporation of the organic solvent gives 10.0 g of crude product. HPLC purification affords 4.6 g of a white solid which when recrystallized from toluene affords white crystals, m.p. 153°-155° C.

Provenance & Evidence