3-Hydroxybenzaldehyde → 3-Ethoxybenzaldehyde

Participants

Reaction Steps

Combine 3-hydroxybenzaldehyde (5.6 g, 46 mmol) and 1-iodoethane (10.7 g, 69 mmol) in DMSO (25 mL) and warm to 80° C. Treat with of cesium carbonate (22.4 g, 69 mmol) in portions. During the addition the temperature begin to rise so the bath is removed. Stir the reaction at 80° C. for 1 hour, pour into 200 mL brine and extract twice with 150 mL diethyl ether. Wash the combine extracts twice with 200 mL brine, dry over MgSO4 and concentrate under vacuum to give an oil. Purification by chromatography (SiO2; 2.5% EtOAc in hexanes) affords 5.73 g (38 mmol; 83%) of the title compound as an oil: 1H NMR (CDCl3) 9.94 (s, 1H), 7.42–7.41 (m, 2H), 7.36–7.35 (m, 1H), 7.16–7.13 (m, 1H), 4.10–4.04 (q, 2H), 1.64–1.40 (t, 3H).

Provenance & Evidence