4-Chlororesorcinol → 5-chloro-6-hydroxybenzofuran-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of 4-chlororesorcinol (4.34 g, 30.0 mmol) in nitrobenzene (60 mL) was added with aluminum chloride (10.2 g, 90.0 mmol) at room temperature. Then, the mixture was added with chloroacetyl chloride (2.87 mL, 36.0 mmol) under ice cooling. The reaction mixture was stirred at 40° C. for 2 hours, and then added with 2 N aqueous sodium hydroxide (60 mL), and the aqueous layer was separated. The separated aqueous layer was added with concentrated hydrochloric acid and thereby adjusted to pH 3, and the precipitated solid was collected by filtration to obtain the objective 5-chloro-6-hydroxybenzofuran-3(2H)-one (0.995 g, 17%).

Provenance & Evidence