2,4-Dihydroxybenzaldehyde → 4-Benzyloxy-2-hydroxybenzaldehyde

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Reaction Steps

To solution of 2,4-dihydroxybenzaldehyde (160 g, 1.16 moles) in acetonitrile (2 L) was added potassium fluoride (134 g, 2.30 moles) and benzyl chloride (257 g, 2.03 moles). The reaction was heated to reflux and the volume of solvent was reduced by distillation to approximately half of original over the period of 24 hours. When less than 8% of starting material remains as observed by HPLC the residual acetonitrile is evaporated at reduced pressure and the residue was suspended in water. The aqueous mixture was extracted with ethyl acetate several times and the combined extracts were washed with potassium carbonate, hydrochloric acid and brine. Evaporation of the organic solvent at reduced pressure afforded the crude product in 76% yield. If needed, the product may be recrystallized from t-butyl methyl ether and hexane.

Provenance & Evidence