1,3-Dimethoxybenzene → 1,3-Dimethoxy-2-propylbenzene

Participants

Reaction Conditions

Reaction Steps

1,3-Dimethoxybenzene (20 g, 145 mmoles) in 200 ml of dry tetrahydrofuran was cooled to -10° C. To this solution at -10° C. was added n-butyllithium (100 ml of a 1.6 M solution in hexane, 160 mmoles) over 20 minutes. The reaction was then stirred for 2.5 hours at 0° C. At 0° C., propyl iodide (24.65 g, 145 mmoles) was added slowly over 15 minutes. When the addition was complete, the reaction was allowed to warm to room temperature and stirred overnight. After stirring overnight, the reaction was refluxed for 1.5 hours, then cooled to room temperature and quenched with ice. The tetrahydrofuran was removed under vacuum, and the resulting aqueous layer was extracted several times with diethyl ether. The organic extract was dried over magnesium sulfate and filtered to give a clear oil after solvent removal (26.11 g). The oil was purified by vacuum distillation to provide the title intermediate (24.0 g, 92%).

Provenance & Evidence