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

Participants

Reaction Conditions

Reaction Steps

1,3-Dimethoxybenzene (20 g, 145 mmol) in 200 mL of dry tetrahydrofuran was cooled to -10° C. To this solution at -10° C. added nBuLi (100 mL of a 1.6M solution in Hexane, 160 mmol ) over 20 min. The reaction was then stirred for 2.5 hours at 0° C. At 0° C., propyliodide (24.65 g, 145 mmol ) was added slowly over 15 min. 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 hour then cooled to room temperature and quenched with ice. The THF was remove under vacuum, and the resulting aqueous layer was extracted several times with Et2O. The organic extract was dried over MgSO4 and filtered to give a clear oil after solvent removal (26.11 g). The oil was purified by vacuum distillation (24.0 g, 92%).

Provenance & Evidence