Potassium Carbonate → Methyl 3-chloro-4-isopropoxybenzoate

Participants

Reaction Steps

Methyl 3-chloro-4-hydroxybenzoate (available from Pfalz % Bauer, 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 h 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