Triethylamine → 2-Hydroxy-3-pivaloyloxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

A suspension of 2,3-dihydroxybenzaldehyde (15 g, 109 mmole) in CH2Cl2 (70 ml) was cooled to -10° C. Triethyl amine (5.49 g, 54.3 mmol) was added followed by pivaloyl chloride (6.49 g, 53.9 mmol). The reaction was allowed to stir for 1 hour at -10° C. and then warmed to ambient temperature. The reaction mixture was stirred at ambient temperature overnight, then washed with water, 1N aqueous HCl, saturated aqueous NaHCO3 and water. The organic phase was dried (MgSO4) and evaporated. The residue was purified by chromatography (eluant: ethyl acetate/hexane) to give 2-hydroxy-3-pivaloyloxybenzaldehyde: (10.15 g, 84%).

Provenance & Evidence