Hydrochloric Acid → 5-Chloro-salicylaldehyde

Participants

Reaction Conditions

Reaction Steps

64.25 g (0.5 mole) of p-chlorophenol and 55 g (0.2 mole) of trioctylamine are dissolved in 100 ml of toluene. Under N2, 13 g of tin tetrachloride are added dropwise at 0° C. After 20 min at room temperature, 33 g of dried paraformaldehyde are added, and the mixture is heated at 100° C. for 5 hours. After cooling, the mixture is poured onto 2.5 l of H2O, and the mixture is acidified to pH 2 with 2N HCl and extracted with diethyl ether. The ether phase is washed with saturated NaCl solution and dried with Na2SO4 and concentrated. Chromatography on silica gel using ethyl acetate/cyclohexane (1:6) provides 24 g of the title compound, melting point 99° C.

Provenance & Evidence