Potassium Carbonate → Methyl 3-chloro-4-isopropoxybenzoate

Participants

Reaction Steps

Methyl 3-chloro-4-hydroxybenzoate (50 g, 0.27 mole), K2CO3 (74 g, 0.54 mole) and 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 in EtOAc/hexane (1:1) to give the title compound as an oil (55 g, 90%). 1H NMR (400 MHz, CDCl3) δ 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); m/z (API-ES) 229 [M+H]+.

Provenance & Evidence