Methyl 4-hydroxyhex-2-ynoate → HCID 13237261, compound

Participants

Reaction Steps

To a solution of methyl-4-hydroxy-2-hexynoate (25.0 g, 176 mmol) in acetone (200 mL), cooled in an ice water bath, was added Jones reagent (70 mL of 3.2 M chromium VI oxide in 1:3 sulfuric acid:water). The reaction mixture was allowed to stir at room temperature for 3 h then filtered through a plug of diatomaceous earth and the filter cake was rinsed with dichloromethane (2×100 mL). The organic phase was saved and the aqueous phase was extracted with dichloromethane (2×100 mL). The combined organic phases were washed with saturated sodium bicarbonate (2×200 mL), dried (sodium sulfate) and concentrated to provide 17.0 g (69%) of 4-oxo-hex-2-ynoic acid methyl ester.

Provenance & Evidence