Salicylic Acid → 4-Hydroxy-o-toluic acid

Participants

Reaction Conditions

Reaction Steps

50 g (0.36 mole) of hydroxy-benzoic acid are dissolved in methanol in a 1 liter capacity Erlenmeyer. The mixture is cooled to a temperature of about 5° C. Thereafter, 70 ml (1 mole) of acetyl chlorine are added drop by drop and the mixture is left to return to ambient temperature. A magnetic stirring is carried out over a period of about ten hours. The methanol is then flushed out under vacuum, in the same way as the hydrochloric acid that is formed and the remaining acetyl chloride. 55 g of a solid brown product are recovered. At this step, the yield of the reaction is 99%. A recrystallization in ethanol produces 37 g of pure product, the melting point of which is 123° C. The overall yield of the reaction is 67%.

Provenance & Evidence