Methyl 3-oxohexanoate (Methyl Butyrylacetate) is an organic compound commonly used in the manufacture of fragrances, drugs, and other chemicals. It can be used as a condensation reagent, a diazotization reagent and an addition reagent, and it plays a catalytic role in some organic synthesis reactions, and can also play a role in some drug synthesis. In addition, the compound is widely used in the food industry, for example in products such as juices, beer and confectionery.
Butyl chloride (18.0 g, 168.94 mmol) in CHCl3 (50 mL) was added dropwise to a stirred solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (22.14 g, 153.58 mmol) and pyridine (25.0 mL, 307.2 mmol) in CHCl3 (250 mL) at 0 C and stirred for 1 hour. The reaction mixture was allowed to warm to ambient temperature and stirred overnight. Aqueous 1N HCl (150 mL) was added and the resulting mixture was extracted with CHCl3 (3 x 150 mL). The combined organic layers were washed with water (2 x 100 mL), dried over Na2SO4, filtered and concentrated. CH3OH (250 mL) was added and the solution was heated to 80 C and refluxed for 3 hours. Concentrated under reduced pressure and distilled to give the title compound as a yellow liquid in yield (17.6 g).
