Methyl iodide → 2,6-Dimethoxytoluene

Temperature

0 °C

To a solution of 1,3-dimethoxybenzene (2.00 g, 14.5 mmol) in THF (30 mL) at 0° C. was added n-BuLi (6.40 mL, 15.9 mmol, 2.5 M in hexanes) slowly over a 2 min period. The solution was stirred at 0° C. for 15 min and then at room temperature for 1.5 h. The solution was re-cooled to 0° C., iodomethane (2.70 mL, 43.5 mmol) was added slowly (the solution warmed up) and the solution was stirred at 0° C. for 10 min and then at room temperature for 1.5 h. The reaction was quenched with water, most of the solvent was removed in vacuo, and extraction was done in EtOAc (2×75 mL) with water (50 mL). Flash chromatography with silica gel (gradient to 6% ethyl ether/hexanes) afforded the title compound as a colorless liquid (1.98 g, 90% yield): 1H NMR (300 MHz, CDCl3) δ 2.10 (s, 3H), 3.82 (s, 6H), 6.54 (d, 2H, J=8.3 Hz), 7.12 (t, 1H, J=8.3 Hz).

1. waitat room temperature for 1.5 h
2. temperatureThe solution was re-cooled to 0° C.
3. temperaturewarmed up) and the solution
4. stirringwas stirred at 0° C. for 10 min
5. waitat room temperature for 1.5 h
6. customThe reaction was quenched with water, most of the solvent
7. customwas removed in vacuo, and extraction

ORD record

ord-6ca57a664aea4ba3a1805fb21a9b89ab

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884814B2