Hydrochloric Acid → Salicylic Acid

Participants

Reaction Steps

Charged were 5.50 g (0.02 mole) of 1-hydroxy-2-carboxy-4-benzylnaphthalene, 50 ml of 1,2-dichloroethane, and as a catalyst, 2.7 g of anhydrous aluminum chloride. The resultant mixture was maintained at 70° C. under stirring. Then, 5.2 g (0.03 mole) of benzyl bromide was added dropwise over 6 hours to conduct a reaction. After completion of the dropwise addition, the reaction mixture was aged for 2 hours at the same temperature and then poured into dilute hydrochloric acid. The resultant mixture was allowed to separate into layers. The lower organic layer was concentrated to obtain 8.2 g of a reddish brown resin. The weight average molecular weight of the resin was 720.

Provenance & Evidence