2-Chloro-1-(5-chloro-2-hydroxyphenyl)ethanone → 5-Chloro-2,3-dihydro-1-benzofuran-3-one

Participants

Reaction Conditions

Reaction Steps

(Ref: J. Org. Chem. 1955; 20; 813-818) A solution of 2-chloro-1-(5-chloro-2-hydroxy-phenyl)-ethanone (5 g; 24.4 mmol) in ethanol was heated to reflux for 10 minutes and sodium acetate (2 g; 24.4 mmol) was added to the hot mixture. Mixture continued to reflux an additional 10 minutes, and reaction was stoppered and chilled to 0° C. for 20 minutes. Mixture was quenched with water and mixture extracted with ethyl acetate (3×75 mL). Combined organics was washed with brine and dried over MgSO4. Crude material was purified by chromatography using 0-1% methanol/DCM to afford 5-chlorobenzofuran-3-one as a oily solid. (3.0 g; 75% yield).

Provenance & Evidence