Methyl iodide → Methyl 5-oxohexanoate

Participants

Reaction Steps

To a rapidly stirred slurry of sodium bicarbonate (25 g) in a solution of 4-acetylbutyric acid (13 g, 0.1 mol) in dimethylformamide (150 ml) was added methyl iodide (47 g). After stirring overnight at room temperature under nitrogen, the reaction mixture was diluted with water (300 ml) and extracted with ethyl ether (250 ml). The organic phase was washed with water and dried over sodium sulfate. The drying agent was filtered and the filtrate concentrated on the rotary evaporator to give 12 g of the title compound as a light yellow oil. The product can be purified by distillation: b.p. 59°-60° (0.1 mm Hg).

Provenance & Evidence