Hydrochloric Acid → Methyl 4-methoxyacetoacetate

Participants

Reaction Conditions

Reaction Steps

In a 2 liter four-necked flask were charged 88.0 g (2.2 mol) of 60% sodium hydride and 753 ml of tetrahydrofuran in a nitrogen stream, and a mixture of 150.6 g (1.0 mmol) of methyl 4-chloro-3-oxo-butyrate and 35.2 g (1.1 mol) of methanol was added thereto dropwise at room temperature (22 to 24° C.). After the addition, the mixture was stirred at room temperature (22 to 24° C.) for 1 hour. The reaction mixture was cooled with ice, and 600 ml (1.2 mol) of 2N hydrochloric acid was added dropwise. The tetrahydrofuran was recovered from the reaction mixture, and 400 ml of toluene was added to the residue. The aqueous phase was extracted with three 200 ml portions of toluene. The organic phase was washed with a 5% sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The residue was distilled under reduce pressure (boiling point: 90° C./1000 Pa) to give 107.7 g (74%) of methyl 4-methoxy-3-oxobutyrate as liquid.

Provenance & Evidence