Chloroacetyl chloride → HCID 86682017, compound

Participants

Reaction Conditions

Reaction Steps

The synthesis was performed with reference to the known literature (Journal of the Pharmaceutical Society of Japan (Yakugaku Zasshi), Vol. 88, p. 589, 1968). A suspension of aluminum chloride (3.5 g, 26 mmol) in nitrobenzene (10 mL) was stirred at 0° C. under an argon atmosphere. This suspension was added with chloroacetyl chloride (1.1 g, 9.9 mmol), and then the mixture was added dropwise with a suspension of 2,6-dihydroxyacetophenone (1.0 g, 6.6 mmol) in nitrobenzene (6.0 mL). After completion of the addition, the reaction mixture was stirred at 50° C. for 17 hours. The reaction mixture was added with ethyl acetate and ice water, the mixture was stirred at room temperature for 1 hour, and then the organic layer was separated. The organic layer was extracted with 1 N aqueous sodium hydroxide, and the aqueous layer was made acidic with 3 N hydrochloric acid to precipitate solid. The precipitated solid was collected by filtration and dried to obtain 7-acetyl-6-hydroxybenzofuran-3(2H)-one (0.90 g, 71%).

Provenance & Evidence