Iodoethane → Methyl 5-acetyl-2-ethoxybenzoate

Participants

Reaction Steps

A stirred mixture of methyl 5-acetyl-2-hydroxybenzoate (10 g, 0.052 mol), iodoethane (16.4 g, 0.104 mol), anhydrous potassium carbonate (14.4 g, 0.104 mol) and 2-butanone (200 ml) was heated under reflux for 3 days. The solvent was then removed by evaporation under vacuum, the residue dissolved in water (200 ml) and this solution extracted with ethyl acetate (4×200 ml). The organic fractions-were combined, washed with brine (2×200 ml), dried (Na2SO4) and evaporated under vacuum, then the residue chromatographed on silica gel (130 g) using a methanol in dichloromethane elution gradient (0-1%). Crystallization of the product from ethyl acetate-hexane gave the title compound as colorless crystals (10.15 g, 88%), m.p. 50°-55° C. Found: C,64.88; H,6.38. C2H14O4 requires C,64.85; H,6.35%.

Provenance & Evidence