Acetone → Dimethyl Sulfate

Participants

Reaction Steps

2,3,6-Trimethyl-4-nitrophenol (2.2 g) and K2CO3 (4.0 g) were added to a flask, to which was slowly added acetone (35 mL), followed by dimethylsulfate (2.09 mL) at room temperature. The suspension was then refluxed for 2.5 hours. After it cooled down, 20 mL water was added and stirred for 15 min. The mixture was taken up by water and ethylacetate and the organic phase was washed with brine, dried and evaporated to give 2-methoxy-1,3,4-trimethyl-5-nitrobenzene as an oil (2.3 g, which still contained 5% dimethylsulfate). 1H-NMR, (300 MHz, CDCl3) δ=7.532, (s, 1H), 3.723, (s, 3H), 2.373, (s, 3H), 2.307 (s, 3H), 2.273 (s, 3H) ppm.

Provenance & Evidence