Hydrochloric Acid → 5-Benzyl-2-hydroxy-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

157 g of sodium hydroxide (50% in water) was added all at once to a stirred mixture of 100 g of p-benzylphenol in 165 ml of ethanol. The mixture was heated to 75°-80° C., and 161.5 g of chloroform was added drop-by-drop to the stirred mixture over a 5-hour period, at 75°-80° C., then was stirred for 2 hours at 75° C. Then 80.8 g of chloroform was added drop-by-drop, at 75°-80° C., and the mixture was stirred for 1 hour at 75° C. This procedure was repeated. The mixture was concentrated under reduced pressure to give a solid residue. The residue was poured into water, and the stirred mixture was acidified with concentrated hydrochloric acid. The aqueous phase was separated, extracted with ether and the extract was concentrated under reduced pressure to give an oil. The oil was extracted with petroleum ether. The extract was concentrated under reduced pressure. The residue was suspended in 150 ml of a saturated solution of sodium bisulfite and the mixture was stirred for 1 hour at room temperature. The liquid was decanted, and the solid was washed with water, stirred with ethanol and the mixture was filtered. The solid was washed with ether, then suspended in 10% sulfuric acid solution. The resulting mixture was stirred for 11/2 hours, then extracted with ether. The extract was dried (MgSO4) and concentrated under reduced pressure to give 5-benzylsalicylaldehyde (1A).

Provenance & Evidence