Isopropyl iodide → Methyl 3-chloro-4-isopropoxybenzoate

Participants

Reaction Steps

Methyl 3-chloro-4-hydroxybenzoate (50 g, 0.27 mole; available from Alfa Aesar), potassium carbonate (74 g, 0.54 mole) and 2-iodopropane (29.5 ml, 0.23 mole) were stirred at room temperature in DMF (100 ml). After 18 hours, the solvent was removed by evaporation under vacuum and the residue was chromatographed over a column of silica 60 eluting with ethyl acetate/hexane (1:1) to give the title compound as an oil (55 g). MS: m/z (API-ES) 229 [MH+]; 1H NMR (400 MHz, CDCl3) δ (inter alia) 8.05 (1H, d), 7.89 (1H, dd), 6.94 (1H, d), 4.60-4.72 (1H, m), 3.89 (3H, s), 1.41 (6H, d).

Provenance & Evidence