3-Hydroxybenzyl alcohol → Aspirin

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Reaction Steps

3-hydroxymethylphenol (10 g, 0.08 moles) is dissolved in toluene (50 ml) containing triethylamine (9.8 g, 0.1 moles). To the so obtained solution, a solution of the acetylsalicylic acid chloride (16 g, 0.08 moles) in toluene (50 ml) is added at the temperature of 5-10° C. under stirring. The mixture is maintained at a temperature within the above mentioned range, under stirring for 2 hours, then poured in water and then extracted with dichloromethane (2×100 ml) The organic phase is separated, washed in sequence with a solution of potassium carbonate at 25% w/v, with water, with a 3% hydrochloric acid solution, and lastly again with water, then anhydrified with sodium sulphate and the solvent evaporated under vacuum. The residue is crystallized from isopropanol. 3-hydroxymethylphenyl ester of the 2-acetoxybenzoic acid (45.8 g, 0.16 moles, yield 80%) is obtained.

Provenance & Evidence