Salicylic Acid → Methyl Salicylate

Participants

Reaction Steps

Combine salicylic acid (19.4 g, 140.5 mmol), sulfuric acid (20 mL), and methanol (100 mL). Heat to reflux. After 18 hours, pour the reaction mixture into dichloromethane. Separate the layers and extract the aqueous layer twice with dichloromethane. Combine the organic layers and extract three times with 5%.aqueous sodium bicarbonate solution. Dry the organic layer over MgSO4, filter and evaporate invacuo to give methyl salicylate: Rf=0.60 (silica gel, 1/10 ethyl acetate/hexane).

Provenance & Evidence