Methyl iodide → Methyl o-toluate

Participants

Reaction Steps

A mixture of o-toluic acid (15 g, 0.11 mole), iodomethane (51 g, 0.36 mole) and anhydrous sodium bicarbonate (25.2 g, 0.3 mole) in dry dimethylformamide (60 ml) was stirred at 70° (oil bath temperature) under an atmosphere of nitrogen for 3.5 hours. The resulting mixture was diluted with water (200 ml) and extracted with ethyl ether (3×100 ml). The combined extracts were washed several times with water, dried over anhydrous MsGO4 and evaporated in vacuo to give the title ester compound (15 g, 90.6%) as an oil with a consistent H1 -NMR spectrum.

Provenance & Evidence