Hydrochloric Acid → 3-(Phenylmethyl)salicylaldehyde

Participants

Reaction Conditions

Reaction Steps

To a warm, stirred mixture of sodium hydroxide (8.0 g) in water (8.00 ml) was added a warmed solution of 2-hydroxydiphenylmethane (1), (4.9 g, 27 mmol) in ethanol (4 ml) and the mixture heated to 65° C. Chloroform (4.1 ml) was added down a water condensor and the resulting mixture began to reflux. After 1 h at reflux, the mixture was cooled in ice, acidified to pH 2 with 1N HCl and extracted with ethyl acetate (3×30 ml). The combined extracts were dried (Na2SO4) and the solvent removed to yield a dark brown gum. The product was eluted through a silica column, using 0-10% ethyl acetate in petroleum spirit to yield a yellow oil (1.33 g, 24%)

Provenance & Evidence