Beta-Propiolactone → HCID 64853602, compound

Participants

Reaction Steps

To a suspension of 2-fluoro-5-methylphenol (1.0 g, 7.9 mmol) in tetrahydrofuran (10 mL) at 0-5° C. was dropwise added potassium tert-butoxide 1N in tetrahydrofuran (8.3 mL, 8.3 mmol), followed by 3-propiolactone (0.55 mL, 8.7 mmol) in one portion. The mixture was warmed to room temperature for 1 hour, then heated at 50° C. for 2 hours. After cooling to room temperature, the mixture was quenched with a saturated solution of sodium hydrogenocarbonate (1 mL) and diluted with water (9 mL). The aqueous layer was washed with ethyl acetate (10 mL), acidified with 1M hydrochloric acid until pH 2 and extracted with ethyl acetate (2×10 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 3-(2-fluoro-5-methylphenoxy)propanoic acid (10a) (0.96 g, 4.8 mol, 60%) which was used without further purification.

Provenance & Evidence