2,6-dimethylphenol
sodium hydride (60 % in mineral oil)
methyl iodide

Sodium hydride (60% in mineral oil) (44.0 g, 1.10 mol) was washed with petroleum ether (3 × 100mL) and then suspended in dry THF (500 ml) and the mixture was cooled to 0 ^oC.  2,6-Dimethylphenol (122 g, 1.00 mol) was then added portion-wise and the reaction was stirred for 30 min.  Methyl iodide (213 g, 1.50 mol) was then added and the reaction heated at reflux for 18 h.  The mixture was allowed to cool and the solvent removed in vacuo.  The residue was partitioned between water (500 ml) and CH₂Cl₂ (3 × 500mL).  The combined organic layers were dried (MgSO₄) and reduced in vacuo to give a yellow oil.  This oil was distilled at atmospheric pressure to afford 2,6-dimethylanisole as a colourless oil (97.9 g, 72%).

bp 182 ^oC (ref 181-182 ^oC); δ_H (200MHz, CDCl₃) 7.04 (2H, d, J 6.5, m-CH), 6.94 (1H, t, J 6.5, p-CH), 3.75 (3H, s, OCH₃), 2.32 (6H, s, CCH₃).

A. W. Baldwin and R. Robinson, J. Chem. Soc., 1934, 1264-1267.