Water → HCID 10798396, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methylresorcinol (3.23 g, 26.02 mmoles), ethyl 2-fluoro-acetoacetate [E. B. Banks, N. J. Lawrence, A. L. Popplewell, J. Chem. Soc., Chem. Commun, 343 (1994)] (3.85 g, 25.99 mmoles) in 0.5 mL of 1,4-dioxane was added dropwise, at 0° C. and under an inert atmosphere, to 25 mL of concentrated sulfuric acid. The reaction mixture was stirred for 1.5 hours, while the temperature was increased to 25° C. Cold water (100 mL) was added, the reaction mixture was stirred for 15 minutes and the resulting precipitate was collected by suction filtration, dried in vacuo, affording 4.56 g (84% yield) of 3-fluoro-4,8-dimethyl-7-hydroxycoumarin as a white solid. An analytical sample was obtained by recrystallisation from methanol:water: mp 260° C. (decomp.).

Provenance & Evidence